Sodium Hydroxide → HCID 68696711, compound

Participants

Reaction Steps

A suspension of 4-[(1H-indole-6-carbonyl)-amino]-benzoic acid tert-butyl ester (200 mg, 0.595 mmol) and tetrabutylammonium hydrogensulfate (20 mg, 0.059 mmol) was treated with 50% aq. sodium hydroxide solution (0.30 mL, 7.4 mmol), then after 5 min 2-methoxy-5-methylbenzenesulfonyl chloride (0.197 mg, 0.892 mmol) was added, and the two-phase mixture was stirred for 1 h at room temperature. The reaction mixture was partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced 4-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid tert-butyl ester (309 mg, 100%). Off-white solid, MS (ISP): m/e 521.3 (M+H).

Provenance & Evidence