Benzenesulfonyl chloride → 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-azaindole (10 g, 84.6 mmol) and tetrabutylammonium bromide (0.81 g, 2.53 mmol) in dichloromethane (211 mL, 0.4 M) at 0° C. was treated with powdered sodium hydroxide (10.15 g, 253.9 mmol). This solution was stirred at 0° C. for 10 min, it was then slowly treated with benzenesulfonyl chloride (16.3 mL, 126.9 mmol). The reaction was allowed to gradually warm to 25° C. and was stirred for 16 h. At this time, the resulting solids were removed by filtration and were washed with dichloromethane (2×50 mL). The filtrate was concentrated in vacuo to afford a yellow solid which was dried under high vacuum for 30 min. At this time, the solids were triturated with hexanes (3×50 mL) to afford 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (19.5 g, 89.2%) as a light yellow solid: 1H NMR (400 MHz, d6-DMSO) δ ppm 8.38 (dd, 1H, J1=4.5 Hz, J2=1.2 Hz), 8.12 (d, 2H, J=7.8 Hz), 8.05 (dd, 1H, J1=7.8 Hz, J2=1.8 Hz), 7.93 (d, 1H, J=3.9 Hz), 7.74-7.59 (m, 3H), 7.32-7.28 (m, 1H), 6.84 (d, 1H, J=3.9 Hz).

Provenance & Evidence