Sodium Hydroxide → 1-(1-Methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

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Reaction Conditions

Reaction Steps

To a solution of ethyl 1-(1-methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (180 mg, 0.654 mmol) in ethanol (5 mL) and THF (1 mL) was added sodium hydroxide (1.090 mL, 3.27 mmol), and the mixture was stirred at 40° C. for 1 h. The volatiles were removed under reduced pressure. The aqueous phase was acidified to pH 3 with aq. 1N HCl. The solid precipitate formed was collected by filtration and dried under high vacuum to give 144 mg (89%) of product, which was used for next reaction without further purification. LCMS E-S (M+H)=248.1 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82-1.12 (m, 3 H), 1.50 (d, J=6.6 Hz, 6 H), 1.78 (m, 2 H), 2.80-3.11 (m, 2 H), 5.09-5.38 (m, 1 H), 7.47-7.72 (s, 1 H), 8.18-8.46 (s, 1 H), 13.82 (s, 1 H).

Provenance & Evidence