(1-Bromoethyl)benzene → 6-Bromo-2-(1-phenylethyl)-isoquinolin-1-one

Participants

Reaction Conditions

Reaction Steps

6-Bromo-1-hydroxyisoquinoline (150 mg, 0.67 mmol, 1.0 equiv), tetrabutylammonium bromide (25 mg, 0.07 mmol, 0.1 equiv), and 1-bromoethylbenzene (160 uL, 0.8 mmol, 1.2 equiv) were combined in toluene (7 mL) and treated with 50% aq. NaOH (2 mL) and the resulting mixture was stirred rapidly while heating to 70° C. After additional stirring for 14 hours, the mixture was diluted with diethyl ether and washed with water 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 2→12% ethyl acetate/hexanes) gave 6-bromo-2-(1-phenylethyl)-isoquinolin-1-one (227 mg, 0.67 mmol, quant.) as a yellowish oil. This isoquinolinone (220 mg, 0.67 mmol) was converted, via Methods 1 and 2, to compound 4 (109 mg, 56%) and isolated as a white solid. [M−H]−=292.1 m/z. Activity: B

Provenance & Evidence