5-(TrifluoroMethyl)-1H-iMidazo[4,5-b]pyridine synthesis

Yield:617678-32-7 65%

Reaction Conditions:

palladium 10% on activated carbon in water; for 24 h;Heating / reflux;

Steps:

2

N-Benzyl-N-(3-nitro-6-trifluoromethylpyridin-2-yl) amine (110 mg, 0.37 mmol) was dissolved in formic acid (25 ml) and 10% Pd/C (25 mg) was added as a slurry in water. The reaction was heated at reflux for 24 h. The reaction was allowed to cool, filtered through celite and evaporated before azeotroping with toluene (2 x 10 ml) to afford a white solid. The solid was partitioned between ethyl acetate and NaHCO3 solution (sat. aq. ). The organics were evaporated and the residue purified by flash chromatography (ethyl acetate-10% methanol/ethyl acetate) to afford the product as a white solid (45 mg, 65%). 1H NMR (400 MHz, Cd13) 8 7.73 (1H, d, J 8), 8. 33 (1H, d, J 8), 8.42 (1H, s), 12.25 (1H, br s); m/z 188 (M+H+).

References:

WO2003/87099,2003,A1 Location in patent:Page/Page column 32