Potassium Carbonate → 1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-N-(1-(2-methoxyethyl)piperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.123 g, 0.25 mmol, prepared according to Example 7, Step B), 1-(2-methoxyethyl)piperidin-4-amine (0.119 g, 0.750 mmol), copper(I)iodide (0.00952 g, 0.0500 mmol), (S)-pyrrolidine-2-carboxylic acid (0.0115 g, 0.100 mmol), K2CO3 (0.173 g, 1.25 mmol), and DMSO (0.5 mL) was stirred at 100° C. for 3 days in a sealed vessel. The reaction was partitioned between EtOAc and water. The phases were separated and the aqueous phase was re-extracted with EtOAc. The combined organic phases were washed with water, dried (Na2SO4), filtered, and concentrated. The crude was purified by preparative TLC (1 mm thickness) eluting with 10% MeOH/CHCl3. Yield: 42 mg (32%). LRMS (APCI+): 100% purity, 220 nm, m/z 521 (M+1) detected.

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