Sodium Sulfite → 2-(5-ethylthio-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.22 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.26 g of 5-ethylthio-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde, 0.18 g of sodium sulfite, 0.31 g of copper(II) chloride (anhydrous) and 2 ml of N,N-dimethylacetamide was stirred at 150° C. for 8 hours. Ethyl acetate and a saturated aqueous sodium bicarbonate solution were poured into the cooled reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate and then combined with the organic layer of the filtrate, and the mixture was washed with water and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, then the resulting residue was applied to a silica gel column chromatography to obtain 0.34 g of 2-(5-ethylthio-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (25)).

Provenance & Evidence