Phenethyl bromide → HCID 66732542, compound

Participants

Reaction Conditions

Reaction Steps

6-Bromo-1-hydroxy-3,4-dihydroisoquinoline (300 mg, 1.33 mmol, 1.0 equiv), tetrabutylammonium bromide (50 mg, 0.13 mmol, 0.10 equiv), and phenethyl bromide (220 uL, 1.6 mmol, 1.2 equiv) were combined in toluene (14 mL) and treated with 50% aq. NaOH (3 mL), and the resulting mixture stirred rapidly while heating to 70° C. After heating for 14 hours, the mixture was diluted with MTBE and washed with water, saturated NaHCO3, and brine. The organic phase was dried over Na2SO4. Addition of silica gel, concentration, and purification of the residue using flash silica gel chromatography (gradient of 3→18% ethyl acetate/hexanes) provided 6-bromo-2-phenethyl-3,4-dihydroisoquinolin-1-one (201 mg, 0.61 mmol, 46%) as a white solid. This isoquinolinone (201 mg, 0.61 mmol) was converted, via Methods 1 and 2, to compound 12 (90 mg, 50%) which was isolated as a white solid. Activity: A

Provenance & Evidence