Sodium hydride → HCID 57612825, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% in mineral oil, 287 mg, 7.17 mmol, 1.2 eq.) in anhydrous DMF (12 mL) is added [6-(2-chloro-phenyl)-2-oxo-1,2-dihydro-pyridin-3-yl]-carbamic acid benzyl ester (15A) (Bernstein, P. R. et. al., J. Med. Chem., vol. 37, p 3313-3326 (1994)) (2.121 g, 5.98 mmol). After being stirred for 30 minutes, the orange solution is cooled to 0° C. and 2-iodo-N-phenethyl-acetamide (1.902 g, 6.58 mmol, 1.1 eq.) is added. The mixture is stirred at room temperature for 3 hours and is quenched with 1 N HCl (8 mL), extracted with ethyl acetate (3×). The organic layer is washed in sequence with 1 N HCl, saturated Na2S2O3, water and brine; is dried over anhydrous Na2SO4 and concentrated. The residue is purified via silica gel chromatography (2-10% ethyl acetate in dichloromethane) to provide compound 15B as a yellow solid (605 mg, 20%):

Provenance & Evidence