Dimethylformamide → HCID 70984742, compound

Participants

Reaction Steps

To a mixture of sodium hydride (60% in mineral oil; 0.013 g, 0.32 mmol) in anhydrous dimethylformamide (1.4 mL, 0.22 mmol) was added dropwise a solution of 2-methyl-1-(2-methylquinolin-8-yloxy)propan-2-ol (Example 259; 0.050 g, 0.22 mmol) in anhydrous dimethylformamide (1.4 mL, 0.22 mmol). The mixture was allowed to stir at ambient temperature for 30 minutes before by addition of iodomethane (0.054 mL, 0.86 mmol), and the resultant mixture allowed to stir at ambient temperature for 12 hours. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water) providing the title compound (0.038 g, 73%).

Provenance & Evidence