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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 520582
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HRID 520582 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=O)C>[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

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), 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (2 g) and Pd(PPh3)4 (0.265 g) were added to DMF (30 ml) under nitrogen. The mixture was heated at 100° C. for 2 days then cooled to RT 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 ISCO Companion, eluting with a gradient of 30-85% 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 to RT
  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 30-85% MeCN (+0.1% TFA)
  6. additionFractions containing desired product
  7. customthe solvent was removed

출처 및 근거

ORD 기록
ord-779275b9e30e465480c0907c4a539919
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09326987B2

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