Methyl 4-aminobenzoate → HCID 68699035, compound

Participants

Reaction Steps

Benzenesulfonyl-2,3-dihydro-1H-indole-6-carboxylic acid (40 mg, 0.13 mmol) was added to a solution of thionyl chloride (63 mg, 0.53 mmol, 4 equiv.) in dichloromethane (5 ml) and DMF (1 ml). The reaction mixture was stirred for 2 hours, then the solvent was removed. The crude acyl chloride was redissolved in dichloromethane (5 ml) and treated with 4-amino benzoic acid methyl ester (80 mg, 0.53 mmol, 4 equiv.). The mixture was stirred for 30 min. at room temperature, then the solvent was removed. The residue was purified by flash chromatography, yielding 4-[(1-benzenesulfonyl-2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester as a white solid, 42 mg (73%). MS (ISP): m/e=437.3 (M+H+.), δH (300 MHz; CDCl3) 8.02-8.09 (4H, m), 7.82 (2H, d), 7.77 (2H, d), 7.45-7.61 (4H, m), 7.21 (2H, d), 3.98 (2H, t), 3.92 (3H, s), 2.97 (2H, t).

Provenance & Evidence