Sodium hydride → HCID 87210765, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.), stirred solution of tert-butyl 6-bromo-5-chloropyridin-2-ylcarbamate (1.00 g, 3.25 mmol) in DMF (13.0 mL) was added 60% dispersion NaH (0.156 g, 3.90 mmol) under Argon. Stirred at 0° C. for 30 mins then added racemic (tetrahydro-2H-pyran-3-yl)methyl 4-methylbenzenesulfonate (1.143 g, 4.23 mmol). The mixture was then allowed to warm to 25° C. and stirring continued for 19 h. The reaction mixture then was diluted with saturated NH4Cl and then extracted with EtOAc (×3). Organics washed with water (×2), saturated brine (×2), then dried (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel; 5% to 15% EtOAc/heptanes) to give racemic tert-butyl 6-bromo-5-chloropyridin-2-yl((tetrahydro-2H-pyran-3-yl)methyl)carbamate (938 mg).

Provenance & Evidence