Month: September 2021

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. 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), 3-pyridineboronic acid (0.13 g, 1.06 mmol), dichlorobis(triphenylphosphine)palladium (II) (31 mg, 0.04 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, 2:1, v/v): (62 mg, 55%); m.p. 81-82 C.; 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.80 (s, 3H), 4.95 (s, 2H), 6.73 (s, 1H), 6.80 (s, 1H), 6.94 (s, 1H), 7.11 (d, J=5.0 Hz, 1H), 7.34 (dd, J=3.0, 4.8 Hz, 1H), 7.54 (s, 1H), 8.00 (s, 1H), 8.15 (d, J=7.8 Hz, 1H), 8.54 (d, J=5.1 Hz, 1H), 8.60 (d, J=4.4 Hz, 1H), 8.89 (s, 1H); 13C NMR (CDCl3) delta 21.62, 37.79, 55.50, 112.38, 114.08, 116.81, 118.15, 119.21, 120.35, 122.59, 123.59, 128.90, 134.30, 134.78, 139.57, 140.71, 141.57, 141.97, 148.02, 149.92, 150.34, 154.99, 160.48.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 624-75-9.

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

Some common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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. name: 1,2-Difluoro-4-iodobenzene

A mixture of methyl indole-5-carboxylate Ij (2 g, 11.4 mmol), l-iodo-3,4-difluoro-benzene Io (1.5 mL, 12.5 mmol), CuI (0.22 g, 1.14 mmol), trans-N, N’-dimethylcyclohexane-l,2- diamine (0.54 mL, 3.43 mmol), and K3PO4 (6.06 g, 28.5 mmol) in toluene (12 mL) was heated at 110 0C for 7 hours. The reaction mixture was diluted with CH2CI2 and filtered. The solution was concentrated and the residue was purified by flash column chromatography (silica gel, 20% EtOAc/heptane) to give Ip (3.0 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64248-58-4, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BIAN, Haiyan; CHEVALIER, Kristen, M.; CONNOLLY, Peter, J.; FLORES, Christopher, M.; LIN, Shu-chen; LIU, Li; MABUS, John; MACIELAG, Mark, J.; MCDONNELL, Mark, E.; PITIS, Philip, M.; ZHANG, Sui-po; ZHANG, Yue-mei; ZHU, Bin; CLEMENTE, Jose; WO2010/124082; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, 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. Recommanded Product: 460-37-7

2.0 g (9:51 mmol) of the compound from Ex. 164A and 3.29 g (23.8 mmol) of potassium carbonate were stirred in 50 ml of anhydrous DMF for 15 min at RT before 3.3 ml (28.5 mmol) 1,1,1-trifluoro-3-iodopropane have been added .Since the conversion was not complete after stirring overnight at RT , further 1.39 g (9:51 mmol) of potassium carbonate with 1.1 ml (9.51 mmol) of 1,1,1-trifluoro-3-iodopropane are added and the mixture was heated for 2 h at 60 C .After cooling to RT was diluted with ethyl acetate and washed successively twice with water and once with saturated sodium chloride solution.After drying over anhydrous magnesium sulfate, was filtered and the filtrate concentrated to dryness.The crude product was purified by chromatography on a silica gel cartridge (Biotage, 340 g silica gel, eluent: cyclohexane / ethyl acetate 24: 1 -> 10: 1).After concentration and drying of the product fractions 2:06 g (70% d. Th.) Of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 460-37-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAERTER, MICHAEL; DELBECK, MARTINA; KALTHOF, BERND; LUSTIG, KLEMENS; LINDNER, NIELS; KAST, RAIMUND; WASNAIRE, PIERRE; SUESSMEIER, FRANK; (372 pag.)TW2016/7950; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

25252-00-0, A common compound: 25252-00-0, name is 2-Bromo-5-iodobenzoic acid, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Oxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo-5-iodo-benzoic acid (49.5 g) in CH2C12 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h. Then, the solution is concentrated under reduced pressure and the residue is dissolved in THF (100 mL). The resulting solution is cooled in an ice-bath and L1BH4 (3.4 g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1 M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2S04) and the solvent is evaporated under reduced pressure to give the crude product. Yield: 47.0 g (99% of theory)

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-Bromo-5-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM VETMEDICA GMBH; REICHE, Dania Birte; JOHNSTON, Laura; MOHREN, Nicole; WO2014/161836; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 108078-14-4,Some common heterocyclic compound, 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, molecular formula is C8H7IO2, 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.

A mixture of 1-iodo-3-methylbenzoic acid, 20-1 , (5 g), 1-benzyl-3~methyl-1 H- pyrazof-5-amine, 20-2, (3.93 g), K2CO3 (2.64 g) and copper powder (0,61 g) in water (20 mL) was heated at reflux overnight. The resulting mixture was cooled to RT. The pH was adjusted to 14 with 1N aqueous NaOH and the mixture was extracted with CH2CI2. Concentrated HCI was added to the aqueous solution to adjust the pH to 3 and the mixture was filtered. The white solid was dried in a vacuum oven at 50 0C to give 20-3 (3.05 g). LCMS: M is 321. Found: MH+ is 322. The solid was used without further purification.

The synthetic route of 108078-14-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; HO, Ginny D; YANG, Shu-Wei; SMITH, Elizabeth M; MCELROY, William Thomas; BASU, Kallol; SMOTRYSKI, Jennifer; TAN, Zheng; MCKITTRICK, Brian A.; TULSHIAN, Deen B.; WO2010/62559; (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. 63262-06-6, name is 1,4-Dibromo-2,5-diiodobenzene, A new synthetic method of this compound is introduced below., Product Details of 63262-06-6

According to the above reaction formula, under nitrogen protection, the purchased 1,4-dibromo-2,5-diiodobenzene (1.00g/2.05mmol),Carbazole (514.29mg, 3.08mmol), potassium hydroxide (230.1mg, 4.10mmol 2,2,6,6-Tetramethyl-3,5-heptanedione (37.80mg, 0.205mmol) and cuprous oxide (29mg, 0.205mmol) were added to 10mL DMF,After heating to 110C for 124 hours, the reaction was extracted three times with 50 ml of saturated brine and 15 ml of dichloromethane.The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using petroleum etherdichloromethane=3:1 (VV) as eluent.1.02 g of white solid product was obtained with a yield of 87.8%.

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; South China University of Technology; Ying Lei; Zhong Zhiming; Li Yuanfeng; Guo Ting; Peng Junbiao; Cao Yong; (11 pag.)CN111116455; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 35674-27-2, A common heterocyclic compound, 35674-27-2, name is 4-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, 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.

Example 1 Preparation of 4-iodo-3-nitrobenzoic Acid Methyl Ester Using Methanol/Sulfuric Acid To a solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in methanol (30 ml) cooled to 0 C., sulfuric acid (3.4 g, 34.6 mmol) is added slowly. The reaction mixture is warmed to room temperature and then refluxed (?70 C.) for 8 hours. After cooling, the reaction mixture is neutralized with solid NaHCO3 and the salts are filtered. The filtrate is evaporated under reduced pressure. To the residue obtained, water (30 ml) is added and the mixture extracted with MTBE (30 ml*2). The combined organic phase is washed with brine, dried using anhydrous sodium sulfate and filtered. After evaporating the solvent under reduced pressure, 4-iodo-3-nitro-benzoic acid methyl ester is obtained as a yellow solid (2.67 g, 85% yield, 98% HPLC).

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; DIVI’S LABORATORIES LIMITED; Divi, Murali Krishna Prasad; Rao, Mysore Aswatha Narayana; Rajuri, Venkataramana; US2013/172618; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 17533-08-3, The chemical industry reduces the impact on the environment during synthesis 17533-08-3, name is 1,2,4-Trifluoro-5-iodobenzene, I believe this compound will play a more active role in future production and life.

General procedure: preparation of 3,3,3-trifluoro-2-hydroxy-1-morpholino-2-phenylpropan-1-one 8b (Table 2, entry 1). To a solution of phenyl iodide 5a (300 lL, 2.68 mmol)in THF (4 mL) at 0 C, isopropylmagnesium chloride in THF (1338 lL,2.68 mmol, 2 M) was added dropwise. After stirring at 0 C for 1 h, a solutionof methyl trifluoropyruvate 7a (273 lL, 2.68 mmol) in THF (3 mL) was addeddropwise at 78 C. The mixture was stirred at 78 C for 1 h and thenwarmed to 0 C, morpholine 6b (350 lL, 4.01 mmol) and isopropylmagnesiumchloride (2.0 mL, 4.01 mmol, 2 M) were added dropwise. At the end of theaddition, the external cooling was removed, and the reaction was aged at roomtemperature overnight. At 0 C, the reaction mixture was quenched with slowaddition of satd. NH4Cl and extracted with EtOAc. The combined organic layerswere dried over anhydrous Na2SO4, filtered, and concentrated in vacuo.Purification by flash chromatography (0-60% EtOAc/hexane) provided thedesired amide

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, 1,2,4-Trifluoro-5-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Meng, Zhaoyang; Butcher, William E.; Tetrahedron Letters; vol. 54; 37; (2013); p. 5133 – 5136;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 112671-42-8,Some common heterocyclic compound, 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, molecular formula is C6H3BrINO2, 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.

The starting material, phenylboronic acid (76.84g, 630.2mmol) was dissolved in a THF(2780ml) in a round bottom flask, 4-bromo-1-iodo-2-nitrobenzene (309.96g,945.3mmol), Pd (PPh3) 4 ( was added 36.41g, 31.5mmol), K2CO3 (261.3g,1890.6mmol), water (1390ml) and the resulting mixture was stirred at 80 C. After the reaction was completed CH2Cl2 and water, the organic layer was dried overMgSO4, and extracted with silicagel column and re-crystallization and the resultingcompound and then concentrated to give 122.68g product (yield: 70%) was obtained.

The synthetic route of 112671-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duksan Neolux Co. Ltd.; Moon, Song Yun; Lee, Son Hui; Park, Jong Cheol; Kim, Dae Song; Lee, Bom Song; Kim, Seok Hyeon; (113 pag.)KR2015/98171; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 1094759-93-9, name is 4-Chloro-5-fluoro-2-iodoaniline, 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 1094759-93-9, SDS of cas: 1094759-93-9

Step C: 2-Amino-5-chloro-4-fluoro-benzonitrile A solution of 4-chloro-5-fluoro-2-iodo-phenylamine (2.5 g, 9.21 mmol) and copper (I) cyanide (1.65 g, 18.4 mmol) in DMA (45 ml) was heated to 130 C. overnight. Most of the DMA was removed under reduced pressure and the remaining residue was diluted with EtOAc and dichloromethane. The slurry was filtered and the filter cake was washed with dichloromethane and EtOAc. The filtrate was concentrated and the remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-85:15) to afford the title compound (1232 mg, 78%) as light red solid. MS (ESI): 169.2 (M-H)-.

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:
Patent; Hoffmann-La Roche Inc.; Ceccarelli, Simona M.; Conte, Aurelia; Kuehne, Holger; Kuhn, Bernd; Neidhart, Werner; Obst Sander, Ulrike; Rudolph, Markus; US2013/116234; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com