Sodium Hydroxide → 6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

Participants

Reaction Conditions

Reaction Steps

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridine (21) (11.07 g 31.2 mmole) was stirred in methanol (105 mL) at 25° C. and 1M sodium hydroxide (35.3 mL) added. The reaction was stirred at 25° C. for 6 hours. Solvent (85 mL) was removed and water (40 mL) added. The mix was left to cool in ice-water for about 1 hour. The product was filtered off, washed with water (×3) and dried in a vacuum desiccator over potassium hydroxide, overnight. The resulting solid was azeotroped with toluene (100 mL) to give the title compound (8.22 g 95%). 1H-NMR (d6-DMSO, 500 MHz): δ 3.90 (s, 3H), 6.69 (d, J=0.95 Hz, 1H), 7.47 (t, J=0.95 Hz, 1H), 7.94 (d, J=0.63 Hz, 1H), 8.18 (s, 1H), 8.50 (d, J=0.95 Hz, 1H), 11.92 (br s, 1H, NH).

Provenance & Evidence