Iodine → HCID 59536335, compound

Participants

Reaction Steps

The 4-trifluoromethylphenyl Grignard reagent was prepared by adding 1-bromo-4-(trifluoromethyl)benzene (1.3 mL, 9.2 mmol) to a suspension of magnesium turnings (240 mg, 10.0 mmol), a catalytic amount of iodine in THF (10 mL) and stirred at RT for 1.5 h. A separate round-bottomed flask containing isoquinoline (1.1 g, 8.3 mmol) in anhydrous THF (10 mL) was charged with ethyl chloroformate (0.88 mL, 9.2 mmol) under a stream of N2 and the mixture was stirred at RT for 15 min, and then cooled to 0° C. The previously made Grignard reagent was then cannulated into this solution dropwise and the reaction mixture was stirred for 1 h at 0° C. followed by 1 h at RT. The reaction mixture was quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography (10% EtOAc in hexanes) to give ethyl 1-(4-(trifluoromethyl)phenyl)isoquinoline-2(1H)-carboxylate as a white solid. MS (ESI pos. ion) m/z: 348 (M+1).

Provenance & Evidence