3-Cyano-4-fluorophenylboronic acid → 5-(8-Amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-2-fluorobenzonitrile

Participants

Reaction Steps

Into a 10 mL microwave vessel were added 3-cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine (100 mg, 0.0003 mol), 3-cyano-4-fluorophenylboronic acid (0.068 g, 0.00041 mol) potassium carbonate (88 mg, 0.00063 mol), Pd(PPh3)4 (40 my, 0.00003 mol), DME/Water (5:1) (5:1, DME:H2O, 1 mL) and the vessel was degassed 3× with N2. The reaction was microwaved on 300 watts, 100° C. for 45 min. The reaction vessel was resubjected to the microwave heating under the same conditions as before for 45 min. Purification by prep TLC using 4% MeOH in DCM eluting twice afforded 54 mg of the title compound as a yellow solid. MS (ES+): m/z 308.11 (100)[MH+]. HPLC: tR=2.14 min (Open Lynx polar—5 min).

Provenance & Evidence