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

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Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloro-5-{4-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}-1H-indole-3-carboxylate (55 mg, 0.22 mmol) in methanol (8 mL) was added 1.0 M aq. 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 as a white solid (5 mg, 9% yield). MS (ES+) 429.1 (M+H)+. 1H NMR (400 MHz, CD3OD): δ 7.90 (m, 2 H), 7.5 (s, 1 H), 7.29 (d, 2 H), 6.92 (d, 2 H), 4.05 (m, 4 H), 3.83 (t, 2 H), 3.58 (t, 2 H), 3.42 (t, 2 H), 2.05 (m, 2 H).

Provenance & Evidence