Dabco → HCID 14091939, compound

Participants

Reaction Steps

n-BuLi (1.6 M in hexane, 13.94 mL, 22.298 mmol) was added dropwise to a cooled (−78° C.) solution of 1,4-diazabicyclo[2.2.2]octane (2.501 g, 22.298 mmol) in dry THF (40 mL) and stirred for 1 h. 2,6-Dichloropyridine (3.684 g, 20.272 mmol) was added portionwise to the reaction mixture while the color of the reaction mixture turned to pale pink. Stirring was continued for 1 h at −78° C. N-methoxy-N-methylbenzamide (3.0 g, 22.298 mmol) in dry THF (10 mL) was added to the reaction mixture dropwise (color changes to orange then slowly to yellow) and stirring was continued for 1 h. After completion of the reaction, the reaction mixture was concentrated and diluted with diethyl ether. The organic layer was washed with water, followed by brine and dried over Na2SO4. Concentration of the organic layer furnished the crude product as a pale yellow oil. The crude compound was purified by column chromatography (3% EtOAc in hexane) to yield the title compound as a colorless solid (0.736 g, 16.1%). [1H-NMR (CDCl3, 300 MHz) δ 7.84-7.76 (m, 2H), 7.74-7.63 (m, 2H), 7.58-7.48 (m, 2H), 7.422 (d, 1H); HPLCA Rt=4.851 min. (94%); LCMS RtA=0.471 min; [M+H]+=251.9]

Provenance & Evidence