1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine → N-[5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide

HRID 1695725Notes

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:26]=[C:27]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:28]([O:31][CH3:32])=[N:29][CH:30]=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>[NH2:23][C:14]1[CH:15]=[C:16]([C:25]2[CH:26]=[C:27]([NH:33][S:34]([CH3:37])(=[O:35])=[O:36])[C:28]([O:31][CH3:32])=[N:29][CH:30]=2)[CH:17]=[C:18]2[C:13]=1[CH:12]=[N:11][N:10]2[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Participants

Conditions

Temperature: 120 °C

Procedure

1-(Phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (4.2 g, 9.63 mmol), N-[5-bromo-2-(methyloxy)-3-pyridinyl]methanesulfonamide (3.25 g, 11.56 mmol) and Pd(PPh3)4 (1.113 g, 0.963 mmol) were weighed into a round-bottomed flask. DMF (30 ml) was added and the reaction was heated at 120° C. for 20 mins. The solvent was removed in vacuo and the crude material (9.8 g) was dissolved in DCM and loaded onto the top of a 750 g RediSep silica cartridge that was then eluted with 0-100% EtOAc/cyclohexane over 10 column volumes using the Companion XL. The product-containing fractions were combined and the solvent removed in vacuo to afford the title compound as a pale yellow solid (2.39 g).

Workup

customThe solvent was removed in vacuo
dissolutionthe crude material (9.8 g) was dissolved in DCM
washwas then eluted with 0-100% EtOAc/cyclohexane over 10 column volumes
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-374961ca9721417f8da787916abe6d8e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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