Category: 1097871-23-2

Synthetic Route of 1097871-23-2, These common heterocyclic compound, 1097871-23-2, name is 1-Chloro-2,5-difluoro-4-iodobenzene, 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.

Copper(I) iodide (69.4 mg, 0.364 mmol), 2-phenylphenol (93.0 mg, 0.546 mmol) and cesium carbonate (1.78 g, 5.46 mmol) were added to a dry flask under nitrogen. Ethyl malonate (1.11 mL, 7.29 mmol) was added to the mixture, followed by l-chloro-2,5-difluoro-4- iodobenzene (1.00 g, 3.64 mmol) in tetrahydrofuran (3.64 mL, 44.9 mmol). The reaction mixture was sealed and heated to 90C. After 12 hours, the reaction mixture was allowed to cool to room temperature and then diluted with saturated NH4Cl and EtOAc. The organic layer was separated, dried and filtered through Celite. The brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane) to give diethyl 2-(4-chloro-2,5-difluorophenyl)malonate (0.65 g, 58%). 1H NMR (400 MHz, CDCl3) delta 7.37 (dd, J = 6.3, 9.3, IH), 7.17 (dd, J = 6.1, 8.9, IH), 4.91 (s, IH), 4.33 – 4.14 (m, 4H), 1.28 (t, J = 7.2, 6H).

The synthetic route of 1097871-23-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; WO2009/6567; (2009); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 1097871-23-2,Some common heterocyclic compound, 1097871-23-2, name is 1-Chloro-2,5-difluoro-4-iodobenzene, molecular formula is C6H2ClF2I, 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.

Step 2: Preparation of (S)-N-(-(4-chloro-2,5-difluorophenyl)(oxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide To an oven-dried 500 mL round bottom flask under a nitrogen atmosphere was added 1-chloro-2,5-difluoro-4-iodobenzene (9.93 g, 36.18 mmol) in 175 mL anhydrous THF. The resulting solution was cooled to -100 C. with a diethyl ether/liquid nitrogen bath, and then n-BuLi solution (1.6M in THF, 22.6 mL, 36.2 mmol) was added dropwise so that the internal temperature remained between -90 and -100 C. The resulting yellow colored mixture was stirred between -90 and -100 C for 30 min and then (S,E)-2-methyl-N-(oxetan-3-ylmethylene)propane-2-sulfinamide (7.53 g, 39.80 mmol) in 15 mL THF was added dropwise via syringe so that the internal temperature remained between -90 and -100 C. The resulting mixture was stirred between -90 and -100 C. for 30 min and then quenched at the same temperature by dropwise addition of saturated NH4Cl solution followed by warming to room temperature. The mixture was diluted with 150 mL water and 150 mL EtOAc. The layers were shaken and separated and the organic phase was washed with saturated NaCl solution, dried over Na2SO4, and concentrated to a viscous nearly colorless oil which was purified by MPLC using silica gel (0-100% ethyl acetate/hexanes) to provide the desired single diastereomer (6.88 g, 20.38 mmol) as a white foam. LCMS-APCI (POS.) m/z: 338.1 (M+H)+

The synthetic route of 1097871-23-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1097871-23-2, These common heterocyclic compound, 1097871-23-2, name is 1-Chloro-2,5-difluoro-4-iodobenzene, 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.

49-(4-methoxy)-10 borate 1 mmol,1-mmol-4-iododifluorobenzene 1 mmol, tetrakis(triphenylphosphine)palladium 0.1 mmol, toluene 40 mL,10 mL of ethanol and 340 mmol of K2CO (formed as a solution with 10 mL of distilled water) were added to the reaction flask, and then the system was evacuated and protected with nitrogen.The reaction was carried out at 100 C for 12 hours.After the end of the reaction, extraction, rotary distillation, column chromatography (eluent: n-hexane / dichloromethane = 1:1),Recrystallization gave the product A7.The yield was 69%.5A70.5mmol, boranoic acid pinacol ester 1.5mmol,Palladium acetate 0.05 mmol, 2-dicyclohexylphosphine-2′, 6′-dimethoxybiphenyl 0.1 mmol,1.5 mmol of potassium acetate and 25 mL of 1,4-dioxane were added to the reaction flask.The system is then evacuated, protected by nitrogen, and reacted at 90 C for 12 hours.After the reaction is over, extract, spin,Column chromatography (eluent: n-hexane / dichloromethane = 2:1),Recrystallization gave the product B7.The yield was 65%.6 The final product g is obtained by Suzuki coupling reaction:B70.25mmol, the product obtained in step 2, namely 9-bromo-10-(4-cyano)benzoquinone 0.21mmol,Catalyst tetrakis(triphenyl)phosphine palladium 0.03 mmol,Toluene 15mL, ethanol 5mL, K2CO38.4mmol (formed into solution with 5mL distilled water),It was added to the reaction flask and refluxed at 100 C for 12 h under the protection of nitrogen.After the reaction is completed, methanol is washed with hot water, suction filtered, and toluene is recrystallized.Sublimation gives the final product.The yield was 58%.The molecular formula is C48H29F2NO

The synthetic route of 1097871-23-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi Normal University; Hu Jianyong; Zhang Jiali; Zhao Zhen; (25 pag.)CN109678759; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 1097871-23-2, 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. 1097871-23-2, name is 1-Chloro-2,5-difluoro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of (S)-N-((S)-(4-Chloro-2,5-difluorophenyl)(3-fluorooxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide To an oven dried, 100 mL, round bottom flask, under a nitrogen atmosphere, was added 1-chloro-2,5-difluoro-4-iodobenzene (2.41 g, 8.77 mmol) in anhydrous THF (35 mL). The resulting solution was cooled to -100 C. with an ether/liquid nitrogen bath, and then n-butyllithium (1.6M in hexanes, 5.48 mL, 8.77 mmol) was added dropwise, keeping the internal temperature between -90 and -100 C. The resulting yellow mixture was stirred between -90 and -100 C. for 30 minutes, and then (S,E)-N-((3-fluorooxetan-3-yl)methylene)-2-methylpropane-2-sulfinamide (2.0 g, 9.65 mmol) in THF (5 mL) was added dropwise via syringe, keeping the internal temperature between -90 and -100 C. The resulting mixture was stirred between -90 and -100 C. for 30 minutes and then quenched at the same temperature by dropwise addition of saturated ammonium chloride (25 mL). The mixture was diluted with water (50 mL) and ethyl acetate (50 mL). The layers were shaken and separated and the organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated to a viscous nearly colorless oil which was purified with silica gel using a gradient to 50% ethyl acetate/hexanes providing (S)-N-((S)-(4-chloro-2,5-difluorophenyl)(3-fluorooxetan-3-yl)methyl)-2-methylpropane-2-sulfinamide (1.64 g, 4.6 mmol) the desired single diastereomer, as a white foam. 1H NMR (400 MHz, Methanol-d4) delta 7.58-7.37 (m, 2H), 5.28 (d, J=26.1 Hz, 1H), 4.99-4.89 (m, 1H), 4.85-4.76 (m, 1H), 4.69-4.50 (m, 2H), 1.21 (s, 9H). LCMS-ESI (POS.) m/z: 356.10 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 1-Chloro-2,5-difluoro-4-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com