Methyl iodide → HCID 67320191, compound

Participants

Reaction Steps

To a solution of 500 mg (2.17 mmol) (5-chloro-4-fluoro-2-nitro-phenyl)-cyclopropyl-amine (J. Med. Chem. 1992, 35(8), 1385) in 5 mL N,N-dimethylformamide was added 104 mg (2.385 mmol) sodium hydride (60% dispersion in mineral oil) and 339 mg (2.385 mmol) methyl iodide. The reaction mixture was stirred for 6 hours at room temperature and then poured on 30 mL 10% aqueous sodium bicarbonate solution and 30 mL ethyl acetate. The layers were separated and the aqueous layer was extracted a second time with 30 mL ethyl acetate. The organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate 100:0 to 80:20) to give 433 mg (82%) of the desired compound as a yellow oil. MS (ESI): m/z=245.049 [M+H]+.

Provenance & Evidence