3-Bromopyridine → HCID 20346357, compound

Participants

Reaction Conditions

Reaction Steps

7.36 g of 1-methyl-5-chloro-1,3-dihydro-imidazo-(4,5-b)-pyridin-2-one were dissolved in 160 ml of hot dimethylformamide and after cooling the solution to 30° C., 4.64 g of a 50% sodium hydride-oil suspension were slowly added thereto. The mixture was stirred at 40°-50° C. for 2 hours and then 80 ml or 128.8 g of 3-bromo-pyridine and 1.5 g of cuprous chloride were added thereto. The mixture was refluxed for 9 hours and was then cooled and evaporated to dryness. The residue was taken up in ammonium hydroxide solution and was filtered. The product was washed with water to obtain 8 g of raw product which was dissolved in acetone. The solution was chromatographed over silica gel and was eluted with acetone. The product was crystallized from 95% ethanol to obtain 5 g of 1-methyl-3-(3-pyridyl)-5-chloro-1,3-dihydro-imidazo-(4,5-b)-pyridin-2-one in the form of white needles melting at 206°-208° C.

Provenance & Evidence