Sodium Iodide → 6-Bromo-2-(3-hydroxy-2,2-dimethylpropyl)isoquinolin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromoisoquinolin-1(2H)-one (Example 1b, 2.5 g) dissolved in NMP (20 mL) was treated with cesium carbonate (7.27 g) and 3-bromo-2,2-dimethylpropan-1-ol (2.75 mL) under nitrogen. The resulting mixture was stirred at 100° C. for 8 h. Further cesium carbonate (1 eq), 3-bromo-2,2-dimethylpropan-1-ol (1 eq) and water (5 mL) were added and the resulting mixture was stirred at 130° C. for 10 h. The incomplete reaction was diluted with water and extracted with ethyl acetate. The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was dissolved in NMP (20 mL) was treated with cesium carbonate (7.27 g) and 3-bromo-2,2-dimethylpropan-1-ol (2.75 mL) and sodium iodide (0.167 g) under nitrogen and heated at 130° C. for 10 h. The reaction mixture was diluted with water (250 mL), and extracted with ethyl acetate (300 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by (SiO2 chromatography, elution 60% diethyl ether in isohexane) to afford the subtitle compound (0.93 g) as a solid.

Provenance & Evidence