Methyl iodide → HCID 59722598, compound

Participants

Reaction Steps

Iodomethane (9.0 μL, 0.15 mmol) was added to a solution of tert-butyl (6S,9R)-3-[cyclopropyl(hydroxy)methyl]-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (66 mg, 0.15 mmol) and sodium hydride (60% dispersion in mineral oil; 8.3 mg, 0.23 mmol) in tetrahydrofuran (1 mL) at 0° C. After 1 h, the mixture was allowed to warm to ambient temperature. After 2 h, additional iodomethane (6.0 μL, 0.10 mmol) and sodium hydride (60% dispersion in mineral oil; 3.0 mg, 0.08 mmol) were added. After 1 h, the reaction was quenched with water and the mixture was extracted with dichloromethane (3×). The organic layer was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (23 mg). MS 448.2 (M+1).

Provenance & Evidence