Sodium Hydroxide → 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acid

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Reaction Steps

Aqueous sodium hydroxide (1.0 N, 0.66 mL, 0.66 mmol) was added to a solution of methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (80 mg, 0.22 mmol) in a mixture of tetrahydrofuran (3 mL) and methanol (1 mL). After 1 hr, the organic solvents were removed on the rotary evaporator. The residue was diluted with water to bring most of the solid into solution and sufficient 1.0 N aqueous HCl was added to bring the pH of the mixture to about 3. After stirring for 0.5 hr, the precipitate was collected, washed with water, and dried under vacuum over solid sodium hydroxide to give 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylic acid (74 mg, 0.212 mmol, 96% yield) as an orange solid. MS (ESI) m/z 350.2 (M+H). 1H NMR (DMSO-d6) δ ppm 8.52 (1H, d, J=8.54 Hz), 8.17 (1H, s), 8.09 (2H, d, J=8.85 Hz), 7.07 (2H, d, J=8.85 Hz), 6.78 (1H, d, J=8.24 Hz), 4.02 (3H, s), 3.83 (3H, s).

Provenance & Evidence