2-Bromopyridine → HCID 57425669, compound

Participants

Reaction Conditions

Reaction Steps

N-Methoxy-N-methyl-2-morpholin-4-yl-2-phenylacetamide (215 mg, 0.813 mmol) was dissolved in 10 mL of dry THF and cooled to −78° C. In a separate flask, 2-bromopyridine (97 μL, 1.0 mmol) was dissolved in 5 mL of dry THF and cooled to −78° C., to which was added tert-Butyl lithium (1.20 mL, 1.7M solution in pentane, 2.0 mmol) dropwise. After stirring for 30 minutes, the mixture transferred to the amide flask dropwise and stirred for approximately one hour. The mixture was quenched with NaHCO3(sat), warmed to ambient temperature and poured into water. The aqueous layer was extracted 3× with EtOAc and the combined organic extracts were dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100/0/0 to 9/1/0.1 CH2Cl2/MeOH/NH4OH), providing partially purified titled product. The residue was further purified by preparative reverse phase HPLC. The appropriate fractions were poured into NaHCO3(aq sat) and extracted twice with EtOAc. The combined organic extracts were dried with Na2SO4, filtered and concentrated in vacuo to provide 2-morpholin-4-yl-2-phenyl-1-pyridin-2-ylethanone. ESI+MS: 283.1 [M+H]+.

Provenance & Evidence