Methanol → HCID 87158984, compound

Participants

Reaction Conditions

Reaction Steps

KHMDS (0.23 mL (0.91M), 0.21 mmol) was added to a solution of 7-chloro-6-hydroxy-2-(4-methylpyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (87A: 50 mg, 0.1736 mmol) in THF (5 mL) at −78° C. and stirred at −10° C. for 20 minutes, then cooled to −78° C., followed by the addition of N-phenyl trifluoromethanesulfonamide (68.2 mg, 0.190 mmol). The resulting mixture was stirred at room temperature for 60 minutes. The reaction was monitored by TLC (5% methanol in CHCl3). The reaction mixture was quenched with saturated NH4Cl solution and partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 50 mg of the product (70% yield).

Provenance & Evidence