tert-Butyl acetate → HCID 22648123, compound

Participants

Reaction Conditions

Reaction Steps

To 25 mL of THF at −78° C. was added 26.6 mL of a 1.0M solution of lithium hexamethyldisilazane in THF. t-Butyl acetate (4.47 mL) was added dropwise to the cold solution, and the mixture was stirred for 10 min at −78° C. 4,6-Dibromo-3-(bromomethyl)-2-(2-chlorophenyl)pyridine (9.74 g) in 25 mL of THF was added dropwise over 15 min. The mixture was stirred 20 min at −78° C., then quenched by addition of 5 mL of saturated aqueous NaHCO3. The mixture was warmed to rt, diluted with 200 mL of saturated aqueous NaHCO3, and extracted with 3×100 mL of EtOAc. The combined organics were washed with 100 mL of brine, and dried over MgSO4. The residue was purified by flash chromatography on a Biotage 65M column, eluting with a gradient system of 95:5 to 90:10 hexanes-Et2O to yield the title compound as a white solid. Mass spectrum (ESI) 476 (M+1).

Provenance & Evidence