Potassium Carbonate → tert-butyl 4-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-1,4-diazepane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (100.0 mg, 0.2040 mmol, prepared according to Example 7, step B), tert-butyl 1,4-diazepane-1-carboxylate (204.3 mg, 1.020 mmol), copper(I)iodide (15.54 mg, 0.08159 mmol), (S)-pyrrolidine-2-carboxylic acid (18.79 mg, 0.1632 mmol), K2CO3 (140.9 mg, 1.020 mmol) and DMSO (10 mL). The reaction mixture was stirred at 100° C. overnight. The reaction was partitioned between EtOAc and H2O. The phases were separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude product. The crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to afford product (110.4 mg, 96.2%). LRMS (APCI pos): m/e 563 (M+1).

Provenance & Evidence