Allyl bromide → methyl 3-(allyl(tetrahydro-2H-pyran-4-yl)amino)-5-chloro-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 5-chloro-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate (1.0 g, 3.3 mmol) in DMF (10 mL), NaH (0.25 g, 10 mmol) was added at 0° C. and the mixture stirred for 20 minutes. 3-bromoprop-1-ene (1.7 g, 14.13 mmol) was added and the mixture was heated at 80° C. for 15 h. On completion, the reaction was quenched with ice cold water and extraction was carried out using DCM. The combined organic layers were dried, concentrated and resulting crude was purified by column chromatography giving the title compound (0.50 g, 44%).

Provenance & Evidence