Sodium Hydroxide → 6-chloro-5-{4-[1-(methylsulfonyl)azetidin-2-yl]phenyl}-1H-indole-3-carboxylic acid

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Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloro-5-{4-[1-(methylsulfonyl)azetidin-2-yl]phenyl}-1H-indole-3-carboxylate (80 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 prep-HPLC to give the title compound (20 mg, 13% yield) as a white solid. MS (ES+) 445.0 (M+CH3CN)+. 1H NMR (400 MHz, DMSO-d6): δ 8.05 (s, 1 H), 7.95 (s, 1 H), 7.65 (s, 1 H), 7.50-7.30 (m, 4 H), 4.70 (m, 1 H), 3.10 (m, 2 H), 2.89 (s, 3 H), 1.90-1.80 (m, 2 H).

Provenance & Evidence