4-Bromo-6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indole → 3-Fluoro-6-{6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-amine

HRID 244702노트

반응식

HRID 244702 반응식
[F:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([Sn](C)(C)C)=[CH:6][C:5]=2[N:4]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=1.Br[C:26]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]2[C:27]=1[CH:28]=[CH:29][N:30]2[S:36]([C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)(=[O:38])=[O:37]>CN(C=O)C.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>[F:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([C:26]3[CH:34]=[C:33]([F:35])[CH:32]=[C:31]4[C:27]=3[CH:28]=[CH:29][N:30]4[S:36]([C:39]3[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=3)(=[O:37])=[O:38])=[CH:6][C:5]=2[N:4]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:3]=1

참가 물질

5

반응물 2

HCID 583563704-Bromo-6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indoleHCID 583564173-fluoro-1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine

생성물 1

HCID 583564523-Fluoro-6-{6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-amine수율 55.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-fluoro-1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (0.65 g, 1.43 mmol), 4-bromo-6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indole (0.69 g, 1.71 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.17 g, 0.14 mmol) in DMF (5 mL) was heated to 120° C. for 18 hr. The mixture was concentrated in vacuo and purified by silica cartridge (100 g) by Flashmaster II using a gradient of cyclohexane and ethyl acetate to give the title compound as an orange solid (0.48 g).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by silica cartridge (100 g) by Flashmaster II

출처 및 근거

ORD 기록
ord-1f4a51058f634b21a08165aac18ad39d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658635B2

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