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

HRID 520507Notes

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-9d5461560f704c6faf62a5b3dee37aa8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326987B2

Reaction notes

Loading…