Sodium Hydroxide → 1-(3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-(3-methyl-1-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone (1.5 g, 3.4 mmol) in ethanol (30 mL) and tetrahydrofuran (60 mL) was treated with an aqueous sodium hydroxide solution (10%, 20 mL). The reaction was stirred at 80° C. for 16 h. Most of the solvent was removed in vacuo. The resulting precipitate was removed by filtration and washed with water (50 mL). The filtrate was concentrated in vacuo. Silica gel column chromatography (30 g, 200-300 mesh, 15% ethyl acetate/petroleum ether) afforded 1-(3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone (0.85 g, 82.2%) as an off-white solid: 1H NMR (300 MHz, d6-DMSO) δ ppm 11.60 (s, 1H), 8.20 (dd, 1H, J1=4.8 Hz, J2=1.5 Hz), 7.96 (d, 1H, J=8.1 Hz), 7.90-7.87 (m, 1H), 7.78 (s, 1H), 7.48-7.46 (m, 2H), 7.09 (dd, 1H, J1=7.5 Hz, J2=5.1 Hz), 6.44 (d, 1H, J=1.8 Hz), 6.24 (d, 1H, J=9.9 Hz), 2.63-2.56 (m, 1H), 2.57 (s, 3H), 1.08-1.02 (m, 6H).

Provenance & Evidence