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 244702Notes

Reaction equation

HRID 244702 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1f4a51058f634b21a08165aac18ad39d
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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