Iodine → 2-Iodo-4-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzenesulfonyl-4-methoxy-1H-pyrrolo[2,3-b]pyridine (1.0 g, 3.47 mmol) in THF (50 mL) cooled in a dry ice-acetone bath was added n-BuLi (2.1M in hexanes, 2.0 mL). The mixture was stirred for 20 minutes, warmed to 0° C. and stirred for an additional 30 minutes, then cooled to −78° C. A solution of iodine (1.06 g, 4.16 mmol) in THF (10 mL) was added dropwise over 5 minutes and the mixture was warmed to 0° C. and stirred for one hour. Water (10 mL) was added followed by 10% aq. Na2S2O3 (10 mL) and stirred for 5 minutes. Ethyl acetate (50 mL) was added and the organic phase was washed with water, saturated aqueous sodium bicarbonate and brine, dried (MgSO4), filtered and concentrated to afford 1.0 g of 1-benzenesulfonyl-2-iodo-4-methoxy-7-azaindole as a yellow solid which was carried forward without further purification. MS m/z 415.

Provenance & Evidence