Dimethyl Sulfoxide → 3,5-dimethyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Dissolve dimethylsulfoxide (0.324 mL, 4.56 mmol) in DCM (10 mL) and cool the solution to −78° C. Add oxalyl chloride (0.239 mL, 2.74 mmol) to the mixture dropwise and stir at −78° C. for 20 min. Add (3,5-dimethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol (0.369 g, 1.82 mmol) in DCM (10 mL) and stir the mixture at −78° C. for one hr. Add triethylamine (1.27 mL, 9.12 mmol) to the mixture and warm to room temperature then stir for 18 hr. Add saturated aqueous sodium bicarbonate and extract the aqueous 3 times with DCM, dry organic solution then filter and concentrate. Purify using silica gel chromatography, eluting with 20:80 hexanes:ethyl acetate to give the title preparation as a yellow solid (0.358 g, 97%). MS (APCI): m/z=202 [M+H]+.

Provenance & Evidence