1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine → 6-(6-Fluoro-1-((4-nitrophenyl)sulfonyl)-1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-amine

HRID 520587Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([Sn](C)(C)C)[CH:15]=[C:14]([NH2:23])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:25]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30]2[C:26]=1[CH:27]=[CH:28][N:29]2[S:35]([C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)(=[O:37])=[O:36]>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:34][C:32]1[CH:31]=[C:30]2[C:26]([CH:27]=[CH:28][N:29]2[S:35]([C:38]2[CH:39]=[CH:40][C:41]([N+:44]([O-:46])=[O:45])=[CH:42][CH:43]=2)(=[O:36])=[O:37])=[C:25]([C:16]2[CH:15]=[C:14]([NH2:23])[C:13]3[CH:12]=[N:11][N:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[C:18]=3[CH:17]=2)[CH:33]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (0.8 g), 4-bromo-6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indole (0.879 g) and Pd(PPh3)4 (0.212 g) in DMF (5 ml) was heated at 120° C. for 18 h. The solvent was removed in vacuo and the residue purified by silica cartridge (100 g) using a gradient of cyclohexane and ethyl acetate to give the title compound as an orange solid, 0.42 g.

Workup

customThe solvent was removed in vacuo
customthe residue purified by silica cartridge (100 g)

Sources & evidence

ORD record: ord-546c6295f29749c88c0feaeba61a9591
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326987B2

Reaction notes

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