Sodium Hydroxide → 6-chloro-5-{4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl}-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloro-5-{4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl}-1H-indole-3-carboxylate (80 mg, 0.22 mmol) in methanol (8 mL) was added 1.0 M aqueous NaOH (2.0 mL, 2.0 mmol). The mixture was stirred at 70° C. for 24 hours. The mixture was adjusted to pH 7 and purified by reverse phase HPLC to give the title compound (25 mg, 28% yield) as a white solid. MS (ES+) 428.1 (M+H)+. 1H NMR (400 MHz, CD3OD): δ 8.41 (br. s, 1H), 8.03 (s, 1H), 7.97 (s, 1 H), 7.56 (s, 1 H), 7.34 (d, 2 H), 6.98 (d, 2 H), 4.12 (t, 2 H), 3.20-2.75 (m, 10 H), 2.70 (s, 3 H), 2.10-2.01 (m, 2 H).

Provenance & Evidence