Methyl iodide → HCID 67291515, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-(3-bromo-phenyl)-4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (5.0 g, 13.06 mmol) in N,N-dimethylformamide (15 mL) was added a 60% dispersion of sodium hydride in mineral oil (1.1 g, 26.1 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 30 min and then iodomethane (2.5 mL, 39.2 mmol) was added to the above mixture dropwise at 0° C. The solution was stirred at 0° C. for 2 h and then extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The yellowish residue was purified by ISCO combi-flash chromatography (gradient elution, 10% ethyl acetate/hexane) to afford 2-(3-bromo-phenyl)-1,4,4-trimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (3.6 g, 70%) as a yellow oil: MS obsd. (ESI+) [(M+H)+] 397.9 & 399.9.

Provenance & Evidence