Potassium Carbonate → 3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

Potassium carbonate (47.1 g) was added to a solution of N-phenylsulfonyl-7-azaindole (1c) (80.0 g) in THF (500 mL) at 0° C. N-Bromosuccinamide (60.6 g) was then added portionwise to the suspension. The reaction mixture was warmed to rt and stirred for 2 days. It was quenched with water and the mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, then dried over Na2SO4 and concentrated. The residue was subjected to silica gel column (eluted with 7:3 dichloromethane/hexane) to give 1-benzenesulfonyl-3-bromo-1H-pyrrolo[2,3-b]pyridine (1d) (50.78 g, 49%). 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=4.8 Hz, 1H), 8.20 (d, J=8.0 Hz, 2H), 7.82 (d, J=8.0 Hz, 1H), 7.78 (s, 1H), 7.62 (t, J=7.6 Hz, 1H), 7.50 (t, J=7.6 HZ, 2H), 7.26 (m, 1H).

Provenance & Evidence