Methyl iodide → HCID 57541247, compound

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethylsilyl)amide (1063 μl, 1.063 mmol, 1 M in THF) was added to a solution of N-methyl-1-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-phenylmethanesulfonamide (250 mg, 0.531 mmol) in THF (5.3 mL) at −78° C. After stirring for 30 minutes at −78° C., the solution was warmed to room temperature and then cooled to −78° C. before adding a solution of methyl iodide (100 μl, 1.594 mmol) in THF (3.75 mL) dropwise. After 2 hours, the reaction was warmed to room temperature, acidified with aqueous ammonium chloride (saturated) and water (75 mL), then extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with brine (50 mL×2), dried over anhydrous Na2 SO4, filtered and concentrated under reduced pressure to afford the title compound as a yellow solid. LRMS (APCI) calculated for C27H24N4O3S [M+H]+, 485.2; found 485.1.

Provenance & Evidence