Ammonium Chloride → 2-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(Z)-2-(2-naphthyl)vinyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

(2-Naphthylmethyl)(triphenyl)phosphonium chloride (454 mg) is dissolved in 5 ml of tetrahydrofuran and cooled to 0° C. under argon, and potassium tert.-butoxide (125 mg) is added, whereupon the colour of the solution turns to dark red. After 10 min of stirring, 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde (200 mg) is added. The mixture is stirred at 0° C. for another 30 min and then slowly warmed to room temperature. After a further 20 min, saturated ammonium chloride solution is added, and the aqueous phase is separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(Z)-2-(2-naphthyl)vinyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (260 mg).

Provenance & Evidence