Sodium Hydroxide → 3-Bromo-4-((1,4-dimethylpiperidin-4-yl)methoxy)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

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Reaction Steps

A mixture of 4-((1,4-dimethylpiperidin-4-yl)methoxy)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (50 mg, 0.16 mmol), sodium acetate (26 mg, 0.3 mmol), and bromine (32 L, 0.6 mmol) in acetic acid (1 mL) was stirred at ambient temperature for 10 minutes. The reaction mixture was diluted with water (1 mL) and basified to pH ˜8 by dropwise addition of 6N sodium hydroxide solution, producing a yellow precipitate. The solid was collected by centrifugation, dissolved in dimethylsulfoxide (2 mL), and purified by preparative HPLC [5-85% methanol in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min] to afford the title compound as a white solid (25 mg, 38%). 1H NMR (500 MHz, d6-DMSO) δ 9.02 (d, J=8.7, 1H), 8.70 (d, J=9.9, 1H), 8.43 (s, 1H), 4.21 (s, 2H), 2.81 (m, 2H), 2.62 (m, 2H), 2.45 (s, 3H), 1.97 (m, 2H), 1.68 (m, 2H), 1.30 (s, 3H), NH signal not observed. LCMS (Method D): RT=8.660 min, M+H+=414.0/416.0.

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