4-Fluorophenylboronic acid → 6-(4-Fluoro-phenyl)-pyrazolo[1,5-a]pyrazine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-2-trimethylsilanyl-pyrazolo[1,5-a]pyrazine (60 mg, 0.23 mmol), 4-fluorophenylboronic acid (40 mg, 0.29 mmol) and PdCl2dppf (10 mg, 0.014 mmol) in CH3CN (1 ml) and 2N Na2CO3 (aq, 1 ml) in a microwave vial was deoxygenated by bubbling N2 through for 20 seconds. The vial was sealed and then stirred and heated at 150° C. in the microwave for 20 minutes. After cooling the reaction mixture was partitioned between CH2Cl2/H2O. The mixture was passed through a phase separating cartridge. The organic layer was evaporated and the residue was purified by chromatography on silica (5→20% EtOAc/Petrol) to give the title compound (14 mg, oil) 1H NMR (400 MHz, CDCl3): 9.15 (1H, d), 8.75 (1H, s), 8.06 (1H, d), 7.98-7.92 (2H, m), 7.24-7.14 (2H, m), 6.84 (1H, d).

Provenance & Evidence