Hydrochloric Acid → HCID 136337171, compound

Participants

Reaction Steps

To THF (5 mL), a 1M solution of ZnCl2 in ether (5.00 mL, 5.00 mmol) was added followed by a 2M solution of cyclohexyl magnesium chloride in ether (2.50 mL, 5.00 mmol). The reaction mixture was stirred overnight at room temperature and the stirring was stopped until all of the precipitate settled to the bottom of the flask. In a different flask, THF (4 mL) was added to a mixture of palladium acetate (11.8 mg, 0.053 mmol), Ru-Phos (48.9 mg, 0.105 mmol) and 1-(6-bromo-7-fluoro-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.200 g, 0.525 mmol) and purged with nitrogen for 5 minutes. Then, a solution of cyclohexyl zinc chloride prepared as described above (5.25 mL, 2.62 mmol) was added and the mixture stirred for 18 h. The crude reaction mixture was poured into EtOH (10 mL) and acidified with 6 M aq. HCl (1 mL) slowly. The precipitated product was collected by filtration, triturated with EtOH and filtered again to provide the titled compound (0.110 g, 54%). MS (ESI/Cl): mass calcd. for C20H21FN4O3, 384.2; m/z found, 385.2 [M+H]+.

Provenance & Evidence