Benzyl Bromide → benzyl 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

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Reaction Steps

Benzyl bromide (11 mL/89 mol) is added dropwise to a suspension of 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (27.0 g/93.9 mmol) and potassium carbonate (15.6 g/112 mmol) in 310 mL of DMF. The mixture is stirred at ambient temperature for 2 hours and then run into a saturated aqueous solution of ice-cold NaHCO3. The precipitate formed is filtered, thoroughly washed with water, and dried under vacuum to give 32.6 g of a pale yellow powder (yield: 92%).

Provenance & Evidence