Lithium hydroxide, monohydrate → N-(3-Methoxybenzyl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide (70 mg, 0.14 mmol) was dissolved in THF (4 mL) and LiOH hydrate (42 mg, 1 mmol) was added in water (1 mL). The reaction mixture was heated to 150° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc and the organic layer was washed with 10% citric acid, saturated sodium bicarbonate, and then dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography on silica (50 to 100% EtOAc/hexanes) to give the product as a white solid 30 mg, 0.083 mmol, 59%. 1H NMR 500 MHz (DMSO-d6) 12.00 (1H, s), 8.88 (1H, t), 8.32 (2H, m), 8.01 (1H, s), 7.87 (1H, s), 7.83 (1H, s), 7.26 (2H, m), 6.92 (2H, m), 6.93 (2H, m), 6.82 (1H, d), 4.43 (2H, d), 3.70 (3H, s). MH+ 364.10

Provenance & Evidence