Benzenesulfonyl chloride → HCID 59812174, compound

Participants

Reaction Steps

To a solution of the crude azaindole 26 (prepared in the previous step) in dichloromethane (373 mL) was sequentially added, benzenesulfonyl chloride (12.6 mL, 99.1 mmol), 50% aqueous sodium hydroxide (12.2 mL) and tetrabutylammonium hydrogen sulfate (2.82 g, 8.3 mmol). After 2 h stirring the mixture was partitioned between dichloromethane and saturated brine. The organic extract was dried (MgSO4), filtered and concentrated to afford the azaindole 27 (24.2 g, 68% from 25) as a tan coloured solid. 1H NMR (400 MHz; CDCl3) δ 6.89-6.92 (m, 2H), 7.01-7.05 (m, 2H), 7.22-7.28 (m, 3H), 7.33-7.37 (m, 1H), 7.45 (dd, J=7.6, 2.0 Hz, 1H), 7.47-7.52 (m, 2H), 7.60 (tt, J=7.6, 1.3 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.85 (s, 1H), 8.20-8.22 (m, 2H) and 8.64 (d, J=2.0 Hz, 1H).

Provenance & Evidence