Benzenesulfonyl chloride → 6-Bromo-1-(phenylsulfonyl)-1H-indazole-4-carbonitrile

HRID 38814Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.[H-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5]2[CH:6]=[N:7][N:8]([S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[C:9]=2[CH:10]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 6-bromo-1H-indazole-4-carbonitrile (5 g, 22.52 mmol) in N,N-dimethylformamide (50 ml) was added, in portions, sodium hydride (1.351 g, 33.8 mmol) and the mixture stirred at 20° C. for 15 mins then cooled to 0° C. when benzenesulfonyl chloride (3.16 ml, 24.77 mmol) was added dropwise. The mixture was stirred at 20° C. for 18 h then concentrated in vacuo and the residue partitioned between water (100 ml) and dichloromethane (100 ml). The organic layer was separated by hydrophobic frit and evaporated in vacuo to give the title compound as a yellow solid (7.94 g).

Workup

additionwas added dropwise
stirringThe mixture was stirred at 20° C. for 18 h
concentrationthen concentrated in vacuo
customthe residue partitioned between water (100 ml) and dichloromethane (100 ml)
customThe organic layer was separated by hydrophobic frit
customevaporated in vacuo

Sources & evidence

ORD record: ord-0a9c05e5ef1e43e8ac235bb79c926a4b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524751B2

Reaction notes

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