Hydrochloric Acid → 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylic acid

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A solution of methyl 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylate (75 mg, 0.19 mmol) in a mixture of THF (3 ml), MeOH (1 ml) and 1 N aqueous sodium hydroxide (3.0 ml, 3.0 mmol) was stirred at room temperature for 24 hr. This was neutralized with 1 N aqueous HCl and the organic solvents were removed on the rotary evaporator. The residue was dissolved in water and acidified to about pH 3 with 1 N aqueous HCl. The mixture was chilled in an ice bath and the precipitate was collected by filtration and dried to give 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylic acid (70 mg) as a yellow solid. MS (ESI) m/z 380.0 (M+H). 1H NMR (DMSO-d6) δ ppm 11.87 (1H, s), 8.64 (1H, br. s.), 8.50 (1H, s), 8.41 (1H, s), 8.36 (1H, d, J=7.93 Hz), 8.11-8.21 (2H, m), 7.96(1H, br. s.), 7.87 (1H, d, J=8.24 Hz), 7.36 (1H, t, J=8.85 Hz), 3.95 (3H, s).

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