Ethanone, 1-[6-(4-methyl-1H-imidazol-1-yl)-3-pyridinyl]- (9CI) synthesis

Yield:810662-41-0 67%

Reaction Conditions:

with potassium carbonate in dimethyl sulfoxide at 110; for 22 h;Product distribution / selectivity;

Steps:

1.A

l-(6-chloro-pyridin-3-yl)-ethanone 5(7.0 g, 45.2 mmof} and 4-methyliminazole 4 (11.1 g, 135.5 mmole) were combined in DMSO (35 mL), followed by addition of K₂C0₃. The mixture was heated at 110^DC for 22 h. The reaction mixture was then cooled to room temperature and poured into ice water (400 mL) with vigorous stirring for 15 min. The resulting precipitate was collected on a filter and washed with water. The resulting material was dried in vacuo to yield 6 as a tan solid (6.1 g, 67%). LC/MS: [m+l]+=202.2, ^lH NMR (DMSOd6) 300 MHz 52.18 (3H,s), 2.63 (3H, s), 7.72 (1H, s), 7.87 (1H, d, J=9.0 Hz), 8.41 (1H, d, J=9.0 Hz), 8.51 (1H, s), 8.98 (1H, s).

References:

WO2011/163636,2011,A2 Location in patent:Page/Page column 53