Ethylene → HCID 86685976, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of zinc dust (130 mg, 1.98 mmol) in THF (2.0 mL) was added 1,2-dibromoethane (0.02 mL). The mixture was heated with a hair dryer until the evolution of ethylene gas was complete. TMS-Cl (0.02 mL) and 2-bromo-1-methyl-1H-imidazole (0.07 mL, 0.66 mmol) were then added to the above suspension and it was allowed to stir at RT for 30 minutes before the addition of 2-(5-bromo-pyridin-3-yl)-6-chloro-3,4-dihydro-2H-isoquinolin-1-one (74 mg, 0.22 mmol, example 7) and Pd(PPh3)4 (14 mg, 0.011 mmol). The resulting reaction mixture was then heated to 90° C. for 6 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×80 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by prep-HPLC to give title compound (12.0 mg, 16.2%) as a white foam. MS: 339.1 (M+H+).

Provenance & Evidence