Ethyl Acetate → HCID 56942730, compound

Participants

Reaction Steps

Boran tri-bromide (0.68 mL, 0.6715 mmol) was added dropwise to a solution of 6-methoxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (11A: 0.120 g, 0.4477 mmol) in DCM (2 mL) at −78° C. over a period of 5 minutes under nitrogen atmosphere. The resulting mixture was stirred at room temperature for 16 hours. The reaction was monitored by TLC (80% ethylacetate in hexane). Since unreacted starting material was observed, a further 1.5 equivalents of boran tri-bromide (0.68 mL, 0.6715 mmol) was added and stirring was continued for a further 3 hours at room temperature. Methanol and saturated NaHCO3 were added to the reaction mixture and diluted with DCM. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (80% ethylacetate in hexane), followed by preparative TLC afforded 0.011 g of the product (9.7% yield).

Provenance & Evidence