Sodium Hydroxide → 1-tert-butyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Participants

Reaction Steps

To a solution of ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (278 mg, 0.922 mmol) in ethanol (30 mL) was added sodium hydroxide (3.69 mL, 3.69 mmol) and the contents heated at reflux for 2 hours. The solvent was removed in vacuo, the residue dissolved in 20 mL of water, and acidifed by addition of acetic acid. The contents were extracted with EtOAc (4×30 ml). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The product was collected as 233 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.12 (m, 4 H), 1.69 (s, 9 H), 2.22-2.41 (m, 3 H), 2.52 (s, 3 H), 7.45 (s, 3 H). LCMS(ES) [M+H]+ 274.2

Provenance & Evidence