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4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine → 1-(Phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-indazol-4-amine

HRID 1615997
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HRID 1615997 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.[C:20]1([S:26]([N:29]2[C:37]3[CH:36]=[C:35]([Sn](C)(C)C)[CH:34]=[C:33]([NH2:42])[C:32]=3[CH:31]=[N:30]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>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.CN(C)C=O>[C:20]1([S:26]([N:29]2[C:37]3[CH:36]=[C:35]([C:2]4[CH:7]=[CH:6][N:5]=[C:4]5[N:8]([S:11]([C:14]6[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=6)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=45)[CH:34]=[C:33]([NH2:42])[C:32]=3[CH:31]=[N:30]2)(=[O:27])=[O:28])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
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참가 물질

5

반응물 2

HCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridineHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine

생성물 1

HCID 670291711-(Phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-indazol-4-amine수율 27.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.546 g, 4.59 mmol), 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (2 g, 4.59 mmol) and Pd(Ph3P)4 (0.265 g, 0.229 mmol) were added to N,N-dimethylformamide (30 mL) under nitrogen. The mixture was heated at 100° C. for 2 days then cooled at room temperature and concentrated in vacuo. The mixture was purified by column chromatography on silica (70 g) eluting with ammonia and methanol in DCM, then again using the Companion technology and eluting with a gradient of 30 to 85% MeCN (+0.1% TFA)/H2O (0.1% TFA). Fractions containing desired product were combined and the solvent was removed to afford the title compound as a brown solid (663 mg).

후처리

  1. temperaturethen cooled at room temperature
  2. concentrationconcentrated in vacuo
  3. customThe mixture was purified by column chromatography on silica (70 g)
  4. washeluting with ammonia and methanol in DCM
  5. washeluting with a gradient of 30 to 85% MeCN (+0.1% TFA)/H2O (0.1% TFA)
  6. additionFractions containing desired product
  7. customthe solvent was removed

출처 및 근거

ORD 기록
ord-31cd56206b064b8789597a63306ff915
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765743B2

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