Tag: M.W=200-300

Synthetic Route of 608-28-6, A common heterocyclic compound, 608-28-6, name is 2-Iodo-1,3-dimethylbenzene, molecular formula is C8H9I, 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.

3-(2,6-Dimethylphenyl)prop-2-yn-1 -ol (32). A 500 mL 3-neck flask fitted with a stir- bar, condenser, and Ar inlet was charged with 2,6-dimethyliodobenzene (21 .6 g, 93.1 mmol), propargyl alcohol (6.78 g, 7.15 mL, 121 mmol), /’Pr2NH (100 mL), and THF (100 mL). The resultant solution was sparged with Ar for 10 min, then Pd(PPh3) (1 .00 g, 0.93 mmol) and Cul (350 mg, 1 .86 mmol) were added. This mixture was heated at 50 C for 1 .5 hr. HPLC analysis showed the reaction to be incomplete. 8 mL more propargyl alcohol was added and the mixture was heated at reflux overnight. The reaction was still incomplete by HPLC analysis. Another 10 mL propargyl alcohol, 500 mg Pd(PPh3) , and 200 mg Cul were added, and the mixture was refluxed for 6 hr. Another 8 mL portion of propargyl alcohol was then added, and the reaction was continued at reflux overnight. The mixture was then cooled, and the solids were filtered off and rinsed with EtOAc (200 mL). The filtrate was concentrated to a dark oil and partitioned with CH2CI2 (500 mL) and saturated NH4CI (250 mL). The organic phase was washed with saturated aqueous NH CI (250 mL) and brine (200 mL) and filtered through phase separation paper. The solution was then filtered through a plug of silica gel. The silica gel was rinsed with CH2CI2 (1 2 L). The combined filtrate was concentrated to 8.5 g of a brown oil. The crude material was chromatographed on silica gel with the product eluting with 10-12% EtOAc in hexanes. The combined fractions were concentrated in vacuo, taken up in CH2CI2 (200 mL), and washed with 5% aqueous Na2S2O3 (200 mL) then brine (200 mL). The solution was filtered through phase separation paper and concentrated in vacuo to give 5.0 g of 32 as an orange solid (32%). 1H NMR (60 MHz, CDCI3): delta 7.3-6.8 (m, 3H), 4.5 (s, 2H), 2.8 (s, 1 H), 2.4 (s, 6H) ppm. HPLC analysis (5:10:85 H2O:A1 :MeOH) showed a purity of greater than 99% with a retention time of 3.7 min

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; ALLERGAN, INC.; EHRING, George R.; GARST, Michael E.; AVEY, JR., Alfred A.; DOLBY, Lloyd J.; ESFANDIARI, Shervin; MACKENZIE, Vivian R.; MARSDEN, Jeremiah A.; MUCHMORE, David C.; WO2013/101926; (2013); A1;,
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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. 170112-66-0, name is 3,4,5-Trifluoroiodobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 3,4,5-Trifluoroiodobenzene

b) 6- (3 ,4,5-trifluorophenyl)- 8- ((2- (trimethylsilyl)ethoxy)methoxy)-3- ((2- (trimethylsilyl)ethoxy)methyl)guinazolin-4(3H)-oneA solution of 6-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 8- ((2-(trimethylsilyl)ethoxy)methoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)quinazolin-4(3H)-one(0.3g, 0.55 mmol) and 1,2,3-trifluoro-5-iodobenzene (0.18 g, 0.71 mmol) in dioxane (5 ml) was treated with bis(diphenylphosphino)feffocene-palladium(II)dichloride (0.04 g, 0.055 mmol). Aqueous 2M potassium carbonate solution (0.5 ml) was added and the reaction mixture was stuffed at 100 C for 16 hours. After extractive workup (ethyl acetate / water) the organic phasewas dried (Na2SO4), adsorbed on silica and chromatographed (silica gel, heptane / ethyl acetate =90:10 to 50:50) and triturated with hexane to furnish the title compound as a white solid (0.06 g,20%).MS: mle= 553.3 [M+H].

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BISSANTZ, Caterina; BONNAFOUS, Rene; BUETTELMANN, Bernd; JAKOB-ROETNE, Roland; LERNER, Christian; RUDOLPH, Markus; WO2014/102233; (2014); A1;,
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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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1,2-Dichloro-4-iodobenzene

General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv), bispinacolatodiboron (254 mg, 1 mmol, 2 equiv), and the appropriate aryl iodide (0.5 mmol). Under an argon atmosphere, freshly distilled DMSO (0.4 mL) and pyridine (0.4 to 1 equiv) were added successively using a syringe. The reaction mixture was heated to 105 C and stirred and stirred for 2 h under argon.

The synthetic route of 20555-91-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pinet, Sandra; Liautard, Virginie; Debiais, Megane; Pucheault, Mathieu; Synthesis; vol. 49; 21; (2017); p. 4759 – 4768;,
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Reference of 35944-64-0, These common heterocyclic compound, 35944-64-0, name is 3-Iodo-4-methylaniline, 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.

To a solution of 3-iodo-4-methylaniline (1 g, 4.29 mmol) in H2O (25 mL) was added H2SO4 (0.5 M, 25 mL). The solution was heated to 80 C. until all solid dissolved. Then the reaction was cooled to 0 C. and NaNO2 (444 mg, 6.39 mmol) was added in small portions. After 2 hr at this temperature, urea (126 mg, 2.1 mmol) was added at 0 C. The solution was allowed to warm up to room temperature and H2SO4 (0.5 M, 25 mL) was added. The reaction was refluxed for 30 min and cooled down to room temperature. The solution was extracted with EtOAc and Et2O and the combined organic phases were dried over Na2SO4, concentrated, and chromatographied to give the pure product v (800 mg, 80%).

Statistics shows that 3-Iodo-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 35944-64-0.

Reference:
Patent; Synta Pharmaceuticals Corp.; US2006/173006; (2006); A1;,
Iodide – Wikipedia,
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Application of 31599-60-7, A common heterocyclic compound, 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, molecular formula is C8H9I, 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.

5-{[6-(l,3-Thiazol-4-yl)pyridin-3-yl]methyl}-255-dihydro- 3H-pyrazolo[4,3-c]cinnolin-3-one (66 mg, 0.18 mmol) was dissolved in degassed NN- dimetliylformamide (1 mL) and copper (I) iodide (35 mg, 0.22 mmol, 1.2 equiv), l-iodo-2,3- dimethylbenzene (51 mg, 0.22 mmol, 1.2 equiv), (+/-)-rralphan5-N,iV-dimethylcyclohexane-lJ2-diamine (78 mg, 0.549 mmol, 3 equiv) and potassium phosphate (0.27 g, 1.3 mmol, 7 equiv) were added. The vessel was sealed and placed into an oil bath preheated at 105 0C for 40 minutes. The mixture cooled to ambient temperature, diluted with water (5 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were washed three times with water and once with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 96:4; chloroform : methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) delta 8.87 (IH, s), 8.69 (IH, s), 8.31 (IH, d, J – 8.2 Hz), 8.16 (2H, m), 7.77 (IH3 d, /= 8.2 Hz), 7.57 (4H, m), 7.28 (IH, m), 7.22 (IH, d, J = 3.9 Hz), 5.90 (2H, s), 2.37 (3H, s), 2.21 (3H,s) ppm; high resolution mass spectrometry (ES+) m/z 465.1499 [(M+H)” ; calculated for C26H2IN6OS : 465.1492] .

The synthetic route of 31599-60-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2010/96338; (2010); A1;,
Iodide – Wikipedia,
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Synthetic Route of 1829-28-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1829-28-3, name is Ethyl 2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a 2-dram vial with a PTFE-lined cap was charged with acetal 1f (1.00 mL, 0.100 M in DCE, 0.100 mmol), ethyl 2-iodobenzoate (111 mg, 0.402 mmol), NBE-CO2Me (23.8 mg, 0.157 mmol), Pd(TFA)2 (3.4 mg, 0.0102 mmol), TFA-Gly-OH (3.4 mg, 0.0199 mmol), AgOAc (66.3 mg, 0.397 mmol), and DCE (1.00 mL). The resulting mixture was heated to 100° C. and stirred for 24 h. After cooling to room temperature, ethylenediamine (0.100 mL) was added, and the resulting mixture was stirred at 23° C. for 2 h. The mixture was filtered through a plug of silica gel, eluting with EtOAc (30 mL), and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (3:1 hexanes/EtOAc eluent) to afford arylation product 3fp (35.4 mg, 62percent yield, Rf=0.16 in 2:1 hexanes/EtOAc) as a colorless oil. 1H NMR: (500 MHz, CDCl3) delta 8.16 (d, J=8.5 Hz, 1H), 8.05 (s, 1H), 7.84 (d, J=8.2 Hz, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.75-7.68 (m, 1H), 7.59-7.54 (m, 1H), 7.49 (app. td, J=7.5, 1.2 Hz, 1H), 7.42-7.33 (m, 2H), 7.28 (s, 1H), 7.20 (s, 1H), 7.07 (s, 1H), 6.32 (s, 1H), 5.40 (d, J=13.2 Hz, 1H), 5.23 (d, J=13.2 Hz, 1H), 4.96 (d, J=11.6 Hz, 1H), 4.86 (d, J=11.6 Hz, 1H), 4.03 (q, J=7.1 Hz, 2H), 3.69 (q, J=7.1 Hz, 2H), 1.40 (s, 9H), 1.15 (t, J=7.1 Hz, 3H), 0.95 (t, J=7.1 Hz, 3H). 13C NMR: (100 MHz, CDCl3) delta 168.9, 159.5, 154.6, 148.6, 142.5, 142.1, 141.8, 138.2, 131.5, 131.3, 130.8, 130.7, 129.92, 129.90, 129.7, 129.1, 128.07, 128.05, 127.5, 127.3, 126.3, 125.8, 125.5, 103.7, 80.2, 70.1, 70.0, 61.1, 45.2, 28.5, 14.1, 13.9. IR: (film) 1698, 1290, 1253, 1151, 758 cm?1.HRMS: (ESI+) m/z calc’d for (M+H)+ [C34H36N2O6+H]+: 569.2646, found 569.2651.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The University of Georgia Research Foundation, Inc; Ferreira, Eric; Li, Qiankun; (47 pag.)US2018/65909; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 627-31-6, 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 627-31-6 as follows.

Methyl 2-(4-bromo-2-nitrophenyl)acetate (2 g, 7.3 mmol, Eq: 1) and 1,3-diiodopropane (2.45 g, 956 mu, 8.03 mmol, Eq: 1.10) were combined with dimethylformamide (20 ml) at 0 C. Sodium hydride (1.17 g, 29.2 mmol, Eq: 4.00) was slowly added. The dark blue reaction mixture was heated to room temperature and stirred for 16h. The reaction mixture was poured into water and extracted with ethyl acetate (3x). The organic layers were combined and washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. (0328) The residue was purified by chromatography on silica gel to afford the desired product as a brown solid (285 mg, 12 %).

According to the analysis of related databases, 627-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GAUFRETEAU, Delphine; HILPERT, Hans; HUMM, Roland; KOLCZEWSKI, Sabine; MUSER, Thorsten; PLANCHER, Jean-Marc; STOLL, Theodor; (63 pag.)WO2017/76932; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 61272-76-2, These common heterocyclic compound, 61272-76-2, name is 4-Fluoro-2-iodoaniline, 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.

V-Benzyl-2~iodo-5~methoxybenzamide (1.61 g, 4.38 mmol), 4-fluoror~2-iodoamline (867 mg, 3.66 mmol), copper (I) iodide (139 mg, 0.73 mmol), and potassium carbonate (1.26 g, 9.12 mmol) were taken up in anhydrous DMSO (24 mL) and the resulting reaction mixture and the resulting reaction mixture was first stirred at 80 C for 2 hours, followed by heating to 135 C for another 16 hours. After cooling to room temperature, the mixture was filtered over celite and concentrated. Tire residue was diluted with an excess of Et?0 and washed with water. The organic layer was dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : Hex = 0: 100 to 100:0; then EtOAc : DCM = 0: 100 to 25:75) to give l0-Benzyl-8-fuoro-2-methoxy-5,10-dihydro-l IH- dibenzo[6,ej[1 ,4]diazepin~ l~one (565 mg, 44%) as a light yellow foam.

Statistics shows that 4-Fluoro-2-iodoaniline is playing an increasingly important role. we look forward to future research findings about 61272-76-2.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164947; (2019); 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. 620-05-3, name is (Iodomethyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7I

General procedure: To a stirred solution of compound 12 (120 mg, 0.25 mmol, 1 equiv.) in THF (10 mL) was added freshly prepared Ag2O (174 mg, 0.75 mmol, 3 equiv.) and MeI (51 muL, 1.25 mmol, 5 equiv.), then the resulting reaction mixture was stirredat 50 C for 3 hours. After been cooled to room temperature, the reaction mixture was filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography (hexanes : EtOAc = 2:1) to give the desired products. Compound 15 (79 mg, 63%): 1H NMR (500 MHz, CDCl3) delta 7.80 (d, J = 7.5 Hz, 2H),7.64 (d, J = 7.5 Hz, 2H), 7.49 – 7.28 (m, 9H), 5.78 (d, J = 8.7 Hz, 1H), 5.20 (dd,J = 31.7, 12.1 Hz, 2H), 5.02 (dd, J = 8.7, 3.1 Hz, 1H), 4.45 (dd, J = 7.1, 1.5 Hz,2H), 4.32 – 4.21 (m, 2H),3.90 – 3.79 (m, 1H), 3.61 (s, 3H), 3.54 – 3.44 (m, 2H), 1.25 (t, J = 7.5 Hz, 3H);13C NMR (126 MHz, CDCl3) delta 169.70, 168.45, 155.83, 143.87, 143.69, 141.34,134.82, 128.57, 128.53, 127.78, 127.12, 125.13, 120.03, 78.77, 67.90, 67.55,67.32, 56.08, 52.08, 47.14, 14.97; HRMS: calculated for C29H30NO7+ [M+H+]: 504.2017; found: 504.2023. Compound 16 (128 mg, 91%): 1H NMR (500 MHz, CDCl3) delta 7.86 – 7.75 (m, 2H), 7.70 – 7.55 (m, 2H), 7.47 – 7.30 (m, 14H), 5.75 (d, J = 8.6 Hz, 1H), 5.22(dd, J = 30.8, 12.1 Hz, 2H), 5.06 (dd, J = 8.6, 2.9 Hz, 1H), 4.95 (d, J = 11.9 Hz,1H), 4.56 (s, 1H), 4.48 – 4.31 (m, 3H), 4.25 (t, J = 7.2 Hz, 1H), 3.64 (s, 3H); 13CNMR (126 MHz, CDCl3) delta 169.55, 168.37, 155.68, 143.91, 143.72, 141.35, 141.32, 136.76, 134.78, 128.62, 128.58, 128.57, 128.23, 128.21, 127.81, 127.15,125.21, 125.17, 120.07, 73.21, 68.01, 67.37, 56.13, 52.17, 47.12, 26.57; HRMS: calculated for C34H32NO7+ [M+H+]: 566.2173; found: 566.2175.

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:
Article; Liu, Long; Wang, Bo; Bi, Cheng; He, Gang; Chen, Gong; Chinese Chemical Letters; vol. 29; 7; (2018); p. 1113 – 1115;,
Iodide – Wikipedia,
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Synthetic Route of 3032-81-3, A common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, molecular formula is C6H3Cl2I, 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 87BN-[(2Z)-3-(3,5-dichlorophenyl)-5-methyl-1,3-thiazol-2(3H)-ylidene]-2,2-dimethylpropanamide; In a 4 mL vial charged with a stir bar, 2,2-dimethyl-N-(5-methyl-1,3-thiazol-2-yl)propanamide (71 mg, 0.35 mmol) was added, followed by copper(I) trifluoromethanesulfonate benzene complex (35 mg, 0.07 mmol), 5-chloro-1,10-phenanthroline (30 mg, 0.14 mmol) and cesium carbonate (126 mg, 0.39 mmol). A loose cap with septum was placed on the vial and the vial was placed under vacuum in a vacuum oven for 30 minutes. The solid mixture was purged with nitrogen gas a couple of times. Then 1,3-dichloro-5-iodobenzene (115 mg, 0.42 mmol) dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the solid mixture. The vial was capped and placed on a heater/stirrer and heated to 120° C. overnight. Then a 1 mL solution of concentrated ammonium hydroxide/water (1:2) was added. The reaction was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (C8, gradient 10-100percent acetonitrile/water/0.1percent trifluoroacetic acid).1H NMR (500 MHz, DMSO-d6/D2O) delta ppm 1.08-1.12 (m, 9H) 2.25-2.31 (m, 3H) 7.41-7.47 (m, 1H) 7.68 (t, 1H) 7.81-7.85 (m, 2H); MS (ESI) m/z 343 (M+H)+.

The synthetic route of 3032-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; US2009/163470; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com