Methyl iodide → N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]-N-methylbenzamide

Participants

Reaction Steps

A round bottom flask equipped with a stir bar and under argon atmosphere was charged with NaH (60% in oil) (0.04 mmol, 1 equiv) and 1 mL of THF. Another vessel containing N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide (Example 3) was diluted with THF and this solution was added to the NaH solution. Lastly, MeI (0.06 mmol, 1.5 equiv) was added and the reaction was stirred 5 hours under argon. The reaction was quenched with water and extracted with EtOAc. The combined organics were subsequently washed with brine and concentrated in vacuo. The residue was taken up in methylene chloride and adsorbed onto silica gel and flash chromatographed using 25% EtOAc/hexanes to elute product. The product fractions were pooled and concentrated in vacuo to afford 7.2 mg of the title compound as a oil.

Provenance & Evidence