Isoquinoline → HCID 23518689, compound

Participants

Reaction Conditions

Reaction Steps

A solution of isoquinoline (645 mg; 5 mmol) in THF (20 mL) is treated with benzyl chloroformate (853 mg; 5 mmol) at 0° C., and the mixture stirred at 0° C. for 1 hour. 2,6-Difluorophenyllithium (prepared from 1-bromo-2,6-difluorobenzene (1.37 g; 7.1 mmol) and n-BuLi (2.5M in hexanes, 2.7 mL; 6.8 mmol at -78° C.) are added to this mixture and the resulting solution stirred at 0° C. for 1 hour and then at room temperature for 2 hours. The reaction is quenched with saturated NH4Cl solution, extracted with ether, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash chromatography over silica gel (elution with hexanes/ether 5;1) to give the product as a colorless oil (0.62 g) LC-MS [MH+] 378.2, RT=3.00 min.

Provenance & Evidence