1-Bromohexane → 6-Bromo-2-(2-phenylpropyl)-isoquinolin-1-one

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Reaction Steps

6-Bromo-1-hydroxyisoquinoline (200 mg, 0.89 mmol, 1.0 equiv), tetrabutylammonium bromide (30 mg, 0.09 mmol, 0.1 equiv), and hexyl bromide (150 uL, 1.1 mmol, 1.2 equiv) were combined in toluene (10 mL) and treated with 50% aq. NaOH (2 mL), and the resulting mixture was stirred rapidly at ambient temperature. After an additional 14 hours of stirring at room temperature, the mixture was diluted with MTBE and washed with water, sat. 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 3-12% ethyl acetate/hexanes) gave 6-bromo-2-(2-phenylpropyl)-isoquinolin-1-one (87 mg, 0.28 mmol, 32%) as white crystals. This isoquinolinone (87 mg, 0.28 mmol) was converted, via Methods 1 and 2, to compound 7 (27 mg, 35%) which was isolated as a white solid. [M−H]−=372.2 m/z. Activity: A

Provenance & Evidence