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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 244706
Notes
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Reaction equation

HRID 244706 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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 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).

Workup

  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

Sources & evidence

ORD record
ord-aea8e50aacea40f5b3f842f58e068114
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658635B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes