Methyl iodide → HCID 59578436, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of DIPA (1.71 mL, 12 mmol) in THF (50 mL) at −78° C. was added 1.6M BuLi (7.5 mL, 12.0 mmol) and the mixture was stirred at −78° C. for 2 h. The LDA solution was cannulated into a solution of 3-bromo-4-chloropyridine (2.117 g, 11 mmol) in THF (50 mL) at −78° C., and the mixture was stirred at −78° C. for 1 h. A solution of N-(cyclopropylmethylene)methanesulfonamide (10 mmol, crude mixture) in THF (50 mL) was added and the mixture was stirred at −78° C. for 1 h. A solution of MeI (0.625 mL, 10 mmol) in THF (10 mL) was added, and the mixture was warmed to room temperature and stirred overnight. Water (0.5 mL) was added and the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a 0-50% EtOAc-heptane gradient to give N-((5-bromo-4-chloropyridin-3-yl)(cyclopropyl)methyl)-N-methylmethanesulfonamide. MS (ESI): m/z 353.0, 355.0 (M+H)+.

Provenance & Evidence