Water → 4-{4-[6-Amino-5-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

4-{4-[6-Amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (0.065 g, 0.14 mmol) (BB3), trifluoromethanesulfonic acid 5-chloro-8-fluoroisoquinolin-3-yl ester (0.040 g, 0.12 mmol), Cs2CO3 (75 mg, 0.23 mmol), and Pd(PPh3)4 (7 mg, 0.006 mmol) were placed in a sealable microwave tube, taken up in 1,4-dioxane (2 mL, 30 mmol) and H2O (0.54 mL, 30 mmol), flushed with nitrogen, sealed and heated in the microwave reactor at 100° C. for 30 minutes. The reaction mixture was diluted with EtOAc washed with water, brine, dried over Na2SO4, filtered and concentrated. The compound was purified by prep-TLC with 5% 7M NH3 in MeOH and DCM mixture yielding the title compound as pale yellow solid. MS (ES+): m/z=523.15/525.12 (100/40) [MH+]. HPLC: tR=3.03 min (ZQ2, polar—5 min).

Provenance & Evidence