Iodoethane → HCID 86694743, compound

Participants

Reaction Steps

To a solution of 202 (600 mg, 1.81 mmol) in DMF (4.5 mL) at 0° C. was added NaH (101 mg, 2.54 mmol, 60% in oil). The reaction was warmed to RT and stirred for 25 min, then re-cooled to 0° C. and iodoethane (0.27 mL, 3.26 mmol) was added. The reaction was warmed to RT and stirred for 5 h. The reaction mixture was partitioned between EtOAc and H2O. The EtOAc extract was washed thrice with water, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography to afford 360 mg (55%) of tert-butyl ethyl((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)carbamate (208): MS (ESI) m/z=360.3 [M+1]+

Provenance & Evidence