3-fluoro-1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine → 3-Fluoro-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridin-5-yl}-1-(phenylsulfonyl)-1H-indazol-4-amine

HRID 520592Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[F:21][C:22]1[C:30]2[C:29]([NH2:31])=[CH:28][C:27]([Sn](C)(C)C)=[CH:26][C:25]=2[N:24]([S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:38])=[O:37])[N:23]=1>CN(C=O)C>[F:21][C:22]1[C:30]2[C:29]([NH2:31])=[CH:28][C:27]([C:2]3[CH:3]=[C:4]4[CH:10]=[N:9][N:8]([S:11]([C:14]5[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=5)(=[O:13])=[O:12])[C:5]4=[N:6][CH:7]=3)=[CH:26][C:25]=2[N:24]([S:36]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)(=[O:37])=[O:38])[N:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

5-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridine (605 mg) in DMF (4 ml) was added to a solution of 3-fluoro-1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (650 mg) in DMF (6 ml), treated with Pd( )Ph3)4 (165 mg) and then heated at 120° C. for 21 h. The solution was allowed to cool, filtered, and then evaporated. The residue was dissolved in chloroform, loaded onto a 100 g silica cartridge which was eluted with 0-100% ethyl acetate:cyclohexane over 60 min using the Flashmaster II. Appropriate peaks were combined and evaporated to give the title compound as a white solid, 0.577 g.

Workup

temperatureto cool
filtrationfiltered
customevaporated
dissolutionThe residue was dissolved in chloroform
washwas eluted with 0-100% ethyl acetate
customevaporated

Sources & evidence

ORD record: ord-eda4a721951c44969e5835bf00fbd650
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326987B2

Reaction notes

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