Tag: M.W=100-200

Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 624-75-9

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (300 mg, 0.89 mmol), phenylboronic acid (0.12 g, 0.974 mmol), dichlorobis(triphenylphosphine)palladium (II) (31 mg, 0.044 mmol) and potassium carbonate (130 mg, 0.89 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled at room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:3, v/v): (166 mg, 74%); m.p. 55-56 C; 1H NMR (CDCl3) delta 2.32 (s, 3H), 3.71 (s, 3H), 5.14 (s, 2H), 6.79 (s, 1H), 6.84 (s, 1H), 6.96 (s, 1H), 7.13 (d, J=4.9 Hz, 1H), 7.41-7.48 (m, 3H), 7.65 (s, 1H), 7.79 (s, 1H), 7.88 (d, J=6.9 Hz, 2H), 8.61 (d, J=5.1 Hz, 1H); 13C NMR (CDCl3) delta21.51, 39.86, 55.25, 110.90, 113.61, 115.61, 119.78, 120.42, 121.24, 121.76, 126.89, 128.78, 129.11, 130.05, 132.90, 139.19, 139.98, 140.77, 149.89, 151.46, 157.75, 159.75.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 7681-82-5,Some common heterocyclic compound, 7681-82-5, name is Sodium iodide, molecular formula is INa, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of complex [Pd(P,P)Cl2] (100 mg, 0.138 mmol) in10 mL of acetone, were added 207 mg of NuaI (1.380 mmol), underinert atmosphere and vigorous stirring. The dark yellow solutionwas stirred at room temperature for 2 h. After acetone wascompletely removed under vacuum, 10 mL of CH2Cl2 were addedto the resulting solid. The mixture was filtered in order to removethe inorganic salts. Subsequent addition of n-hexane (20 mL) to thefiltrate led to the formation of a yellow solid, which was filteredand dried under vacuum. Yield: 103 mg, 82%. HRMS (positiveESI-MS, Fig. S1, Supplementary Material): calcd for C30H35I2NNaO3P2PdSi [M+Na]+ 929.8878, found 929.8898; calcd forC30H35I2KNO3P2PdSi [M+K]+ 945.8617, found 945.8634. IR (KBr,cm1): 513 (s), 558 (m), 693 (s), 741 (s), 869 (s), 1098 (s), 1430(s), 2820 (w), 2931 (w). 1H NMR (300 MHz, CDCl3): d 0.20 (t, 2H,Si-CH2), 1.20 (m, 2H, -CH2-CH2-Si), 1.60, 2.80 (m, 2H, N-CH2),3.40 (s, 9H, Si-OCH3), 7.30, 7.4-8.0 (m, 20H, Harom). 31P NMR(121.5 MHz, CDCl3): d 24.2. UV-Vis (CH2Cl2), [k (nm), e (M1cm1)]: (418, 6800), (292, 23000), (263, 26150).

The synthetic route of 7681-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stamatopoulos, Ioannis K.; Kapsi, Maria; Roulia, Maria; Vougioukalakis, Georgios C.; Raptopoulou, Catherine P.; Psycharis, Vassilis; Kostas, Ioannis D.; Kollar, Laszlo; Kyritsis, Panayotis; Polyhedron; vol. 151; (2018); p. 292 – 298;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 74-88-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 74-88-4, name is Iodomethane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of N-(tert-butoxycarbonyl)-L-isoleucine (1.24 g, 5.4 mmol, 1.0 equiv) in 35 mL THF was cooled to 0 C and slowly treated with NaH (60 % in mineral oil; 0.64 g, 16.1 mmol, 3.0 equiv). CH3I (6.1 g, 42 mmol, 8.0 equiv) was added and the reaction was stirred for 24 h at ambient temperature. Diethyl ether was added and the organic layer was washed with H2O twice. The combined aqueous layers were acidified with citric acid (pH 3) and extracted with EtOAc. The combined organic phases were washed with Na2S2O3 solution and brine and dried over Na2SO4. Removal of the volatiles left the title compound as a colourless oil (1.18 g, 90%). IR 2971 (w), 2934 (w), 2880 (w), 1741 (m), 1694 (s), 1478 (w), 1457 (m), 1436 (m), 1392 (m), 1366 (m), 1332 (m), 1312 (m), 1198 (m), 1143 (s), 1047 (w), 1033 (w), 999 (m), 937 (w), 913 (w), 868 (w), 772 (m), 727 (w). 1H NMR (500 MHz, CDCl3) delta 0.90 (t, J = 7.4 Hz, 3H, H-6), 0.99 (d, J = 6.6 Hz, 3H, H-4), 1.10 (ddd, J = 13.7, 8.9, 7.4 Hz, 1H, H-5a), 1.47 (br s, 10H, H-10/11/12 & H-5b, overlapped), 1.94-2.14 (m, 1H, H-3), 2.86 (s, 3H, H-7), 4.26 (m, 1H, H-2), 9.46 (br s, OH). 13C NMR (125 MHz, (CD3)2SO) delta 10.3 (C-6), 15.8 & 15.9 (C-4), 24.6 (C-5), 27.9 (C-10/11/12), 30.3 & 30.7 (C-7), 32.8 & 33.0 (C-3), 61.4 & 63.0 (C-2), 79.1 (C-9), 154.8 & 155.3 (C-8), 172.1 (C-1). HRMS (ESI) m/z [M-H]- calcd for C12H22NO4- 244.15433, found 244.15495. [alpha]20D +2.6 (c 1.8, CH3CO2H).

The synthetic route of Iodomethane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wunder, Anja; Rothemund, Matthias; Schobert, Rainer; Tetrahedron; vol. 74; 38; (2018); p. 5138 – 5142;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 74-88-4, name is Iodomethane, A new synthetic method of this compound is introduced below., Safety of Iodomethane

3,4-Dimethoxy-5-iodo-benzaldehyde (compound 102, FIG. 1) A mixture of 5-iodovanillin (7 g, 25.18 mmole), potassium carbonate (8.78 g, 63.53 mmole) and iodomethane (6.43 g, 45.30 mmole) was suspended in 60 mL of DMF and stirred at room temperature for 14 hours. The reaction mixture was quenched with water and extracted with diethyl ether. The organic layer was dried over MgSO4, filtered and evaporated in vacuo to obtain a solid which was recrystallized from hexane/ethyl acetate (2:1) (6.28 g, 85.4%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CytoMed, Inc.; US5358938; (1994); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 624-76-0, name is 2-Iodoethanol, A new synthetic method of this compound is introduced below., Product Details of 624-76-0

0.874 g (11.5 mmol) of thioacetic acid was placed in a 100 mL three-necked flask under N2 protection,(10.0 mmol) of 2-iodoethanol and 1.749 g (11.5 mmol) of DBU were slowly added dropwise to the reaction solution. After completion of the dropwise addition, the mixture was left to stand at room temperature After the reaction, the reaction product was passed through a silica gel column (the particle size of the silica gel was 200 to 300 mesh), and the filtrate was collected to give 0.5 g of a yellow oily liquid, i.e., a middle The yield was 42%.

The synthetic route of 624-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liaoning University; Xia, Lin; Zhang, Aixia; Song, Peng; (14 pag.)CN104893710; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 624-76-0, name is 2-Iodoethanol, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 624-76-0, Safety of 2-Iodoethanol

Acetone (4.0 mL) and sat. NaHCO3 aq. (20 mL) were added to a solution of compound 516 (300 mg, 0.640 mmol) in CH2Cl2 (6.0 mL). Then, a solution of Oxone (787 mg, 1.28 mmol) in H2O (10 mL) was dropwise added to this solution at 0 C. The reaction mixture was stirred at room temperature for 3 h. The resulting solution was extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue (310 mg) was dissolved in anhydrous CH2Cl2 (10 mL) under Ar atmosphere, then 2-iodoethanol (0.50 mL, 6.40 mmol) and ZnCl2 (1 M in THF, 0.64 mL, 0.64 mmol) was added to this solution at -78 C. The reaction mixture was stirred at 0 C for 1 h. After being quenched with sat. NaHCO3 aq. at 0 C, the mixture was filtered through a pad of Celite. The filtrate was diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue (488 mg) was purified by column chromatography (silica gel 10 g, n-hexane: EtOAc = 5:1 to 2:1) to give a diastereomixture of 6 as a white powder (353 mg, 84%, 2 steps from 5).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Osawa, Takashi; Dohi, Masakazu; Hitomi, Yuka; Ito, Yuta; Obika, Satoshi; Hari, Yoshiyuki; Heterocycles; vol. 95; 1; (2017); p. 342 – 352;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 624-76-0, name is 2-Iodoethanol, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 624-76-0, Product Details of 624-76-0

N-methylaniline (5mls, 0.05mol) was reacted with 2-Iodoethanol (3.599mls, 0.05mol) and diisopropylethylamine (8.039mls, 0.05mol) in ACN at 70oC for 16 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc to provide the compound as a yellow orange oil (4.48g, 0.03mol, 64.5%yield). 1H NMR (400 MHz, Chloroform-d) delta 7.27 – 7.15 (m, 2H), 6.81 – 6.67 (m, 3H), 3.74 (t, J = 5.8 Hz, 2H), 3.42 (t, J = 5.8 Hz, 2H), 2.92 (s, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Iodoethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bell-Horwath, Tiffany R.; Vadukoot, Anish K.; Thowfeik, Fathima Shazna; Li, Guorui; Wunderlich, Mark; Mulloy, James C.; Merino, Edward J.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2951 – 2954;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C2H2IN

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (320 mg, 0.95 mmol), 3-acetylphenylboronic acid (0.19 g, 1.13 mmol), dichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.05 mmol) and potassium carbonate (131 mg, 0.95 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:2, v/v): (96 mg, 77%); m.p. 65-66 C.; 1H NMR (CDCl3) delta 2.39 (s, 3H), 2.62 (s, 3H), 3.79 (s, 3H), 4.96 (s, 2H), 6.74 (s, 1H), 6.80 (s, 1H), 6.95 (s, 1H), 7.10 (bs, 1H), 7.50 (t, J=7.5 Hz, 1H), 7.56 (s, 1H), 7.94-8.00 (m, 3H), 8.29 (s, 1H), 8.52 (d, J=4.2 Hz, 1H); 13C NMR (CDCl3) delta 21.59, 26.78, 37.77, 55.78, 112.33, 114.14, 116.93, 118.18, 119.32, 120.14, 122.64, 126.60, 128.68, 129.01, 131.39, 137.53, 139.59, 139.72, 140.66, 141.54, 141.93, 150.05, 156.54, 160.45, 197.89.

The synthetic route of 2-Iodoacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 624-76-0 as follows. Quality Control of 2-Iodoethanol

A solution of 2-[(1-methylethyl)oxy]-5-[5-(1 ,2,3,4-tetrahydro-5-isoquinolinyl)-1 ,3,4- thiadiazol-2-yl]benzonitrile hydrochloride (Preparation 56) (50mg, 0.12 mmol) and potassium carbonate (50mg, 0.36 mmol) in DMF (1 ml) was treated with 2- iodoethanol (0.014ml, 0.18 mmol) and the mixture stirred at 8O0C for 2h. The mixture was diluted with water (10ml) and extracted with ethyl acetate (3x 10ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. Purification of the residue by flash chromatography (cyclohexane/methanol: 0 to 5% gradient) gave 5-{5-[2-(2-hydroxyethyl)-1 ,2,3,4-tetrahydro-5-isoquinolinyl]-1 ,3,4- thiadiazol-2-yl}-2-[(1-methylethyl)oxy]benzonitrile (36mg, 71%) as a clear oil. LCMS (Method formate): Retention time 0.85min, MH+ = 421

According to the analysis of related databases, 624-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; BAILEY, James, Matthew; BIT, Rino, Antonio; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; JONES, Katherine, Louise; SMETHURST, Christian, Alan, Paul; WITHERINGTON, Jason; WO2010/146105; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Iodoacetonitrile

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (320 mg, 0.95 mmol), 3-acetylphenyl boronic acid (0.19 g, 1.13 mmol), thchlorobis(triphenylphosphine)palladium (II) (33 mg, 0.05 mmol) and potassium carbonate (131 mg, 0.95 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:2, v/v): (197 mg, 79%); m.p. 73-74 C.; 1H NMR (CDCl3) delta 2.27 (s, 3H), 2.60 (s, 3H), 3.67 (s, 3H), 5.19 (s, 2H), 6.76 (s, 1H), 6.80 (s, 1H), 6.91 (s, 1H), 7.13 (s, 1H), 7.49 (bs, 1H), 7.64 (s, 1H), 7.85 (s, 1H), 7.95 (d, J=5.4 Hz, 1H), 8.04 (d, J=5.7 Hz, 1H), 8.39 (s, 1H), 8.56 (s, 1H); 13C NMR (CDCl3) delta 21.51, 26.78, 39.89, 55.23, 111.03, 113.93, 115.51, 119.76, 119.90, 121.63, 121.77, 126.71, 128.60, 128.76, 129.11, 130.54, 131.45, 132.06, 132.92, 137.52, 139.61, 140.00, 141.09, 149.91, 151.38, 156.47, 159.69, 198.16.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com