Sodium Carbonate → N-[3-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

HRID 45892

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HRID 45892 반응식
Br[C:2]1[C:3]([C:8]2[C:9]([F:27])=[C:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])(=[O:18])=[O:17])[CH:11]=[CH:12][C:13]=2[F:14])=[N:4][N:5]([CH3:7])[CH:6]=1.CC1(C)C(C)(C)OB([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][N:5]1[CH:6]=[C:2]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)[C:3]([C:8]2[C:9]([F:27])=[C:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])(=[O:18])=[O:17])[CH:11]=[CH:12][C:13]=2[F:14])=[N:4]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 67183603N-[3-(4-bromo-1-methyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluorobenzenesulfonamide

생성물 1

HCID 44622139N-[3-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매3회

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온도
110 °C

실험 절차

To a solution of tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) in dimethoxyethane (3 mL), N-[3-(4-bromo-1-methyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluorobenzenesulfonamide (0.14 g, 0.3 mmol) in dimethoxyethane (3 mL) was added and the mixture was insufflated with nitrogen for 5 min. A solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.13 g, 0.63 mmol) in dimethoxyethane (3 mL) was added and the mixture was insufflated with nitrogen for 10 min, then 2 M sodium carbonate solution (2.5 mL) was added and the mixture was heated at 110° C. in a microwave cavity for 3 h. The mixture was cooled and the organic phase was concentrated. The crude oil was purified by flash chromatography (eluant: dichloromethane/ethyl acetate 1:1). The title compound was obtained as a white solid (0.05 g, 36%).

후처리

  1. waitthe mixture was insufflated with nitrogen for 10 min
  2. temperatureThe mixture was cooled
  3. concentrationthe organic phase was concentrated
  4. customThe crude oil was purified by flash chromatography (eluant: dichloromethane/ethyl acetate 1:1)

출처 및 근거

ORD 기록
ord-5560b44fa49d467ab22cf4b43096828a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541575B2

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