ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate → 2-Benzimidazol-2-yl-N-(4-cyano(3-pyridyl))acetamide

Participants

Reaction Steps

LiHMDS (2.5 eq) was added to ethyl 2-benzimidazol-2-ylacetate (1.0 eq) in THF at −78° C. After 1 hour, 3-amino-4-cyanopyridine (0.8 eq) in THF was added. The resulting mixture was allowed to warm to room temperature overnight. The mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The organic layer washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to yield the desired product. LC/MS m/z 278.3 (MH+), Rt 1.88 minutes.

Provenance & Evidence