Benzenesulfonyl chloride → HCID 11133773, compound

Participants

Reaction Steps

To a stirred two-phase mixture of a solution of the above 3-[2-(tert-butyloxycarbonylamino)ethyl]-5-methoxy-1H-indole in dichloromethane (200 ml) and 50% aqueous sodium hydroxide (50 ml) was added tetrabutylammonium hydrogen sulphate (611 mg, 1.8 mmol) and the mixture was stirred for 10 minutes. Benzenesulphonyl chloride (3.52 ml, 27.6 mmol) was added dropwise uia syringe and the mixture was vigorously stirred for 30 minutes. The mixture was diluted with diethyl ether (500 ml), washed with water (100 ml), brine (2×70 ml), dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, dichloromethane-diethyl ether, 90:10) followed by trituration with hexane-diethyl ether (10;1; 100 ml) afforded 1-(benzenesulphonyl)-3-[2-(tert-butyloxycarbonylamino)ethyl]-5-methoxy-1H-indole (7.55 g, 95%) as a white solid; δH (360 MHz, CDCl3) 7.88 (1H, d, J=8.8 Hz), 7.84-7.80 (2H, m), 7.54-7.48 (1H, m), 7.45-7.38 (2H, m), 7.32 (1H, s), 6.96-6.90 (2H, m), 4.55 (1H, br s), 3.82 (3H, s), 3.44-3.36 (2H, m), 2.82 (2H, t, J=6.8 Hz), 1.45 (9H, s).

Provenance & Evidence