Allyl bromide → HCID 58269933, compound

Participants

Reaction Steps

To a solution of 4,6-dibromo-2-chloro-5-methyl-pyridin-3-ylamine (9.3 g, 31 mmol) and tetrabutylammonium bromide (1.0 g, 3.1 mmol) in anhydrous NMP (30 mL) is added NaH (60%, 1.5 g, 37.5 mmol) in one portion at 0° C. The mixture is gradually warmed to room temperature and stirred for two hours, then treated with allyl bromide (3.3 mL, 37.5 mmol) at 0° C., and stirred at 60° C. for three hours. The reaction mixture is cooled and partitioned between EtOAc and water. The organic layer is separated washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Chromatography of the residue on silica gel (Hexane/EtOAc, 10:1) gives allyl-(4,6-dibromo-2-chloro-5-methyl-pyridin-3-yl)-amine.

Provenance & Evidence