Benzenesulfonamide → 6-Chloro-5-(4-methoxyphenyl)-N-(phenylsulfonyl)-1H-indazole-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of benzenesulfonamide (25.6 mg, 0.163 mmol) and potassium tert-butoxide (22.0 mg, 0.196 mmol) in THF (10 mL) was stirred for 10 minutes, and treated with 6-chloro-5-(4-methoxyphenyl)-1H-indazole-3-carboxylic acid p-tolyl ester (64 mg, 0.16 mmol). The reaction mixture was heated to 65° C. for 16 hours, cooled to room temperature and concentrated in vacuo. The residue was partitioned between water (5 mL) and EtOAc (5 mL), and the layers were separated. The organic layer was concentrated in vacuo and the crude material was purified by reverse phase HPLC (Column: Waters Sunfire C18 19×100 mm, 5 μm; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in MeCN (v/v); Gradient: 60:40 A:B linear to 30:70 A:B in 8.5 min to 100% B to 9.0 min, hold at 100% B from 9.0 to 10.0 min. Flow: 25 mL/min) to give the title compound (2.2 mg, 3% yield). MS (ES+) 442.0 (M+1)+. Retention time=3.29 minutes (Column: Waters Atlantis dC18 4.6×50 mm, 5 μm; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in MeCN (v/v); Gradient: 95:5 A:B linear to 5:95 A:B in 4.0 min, hold at 5:95 A:B to 5.0 min. Flow: 2 mL/min).

Provenance & Evidence