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

HRID 604307Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]1[C:16]([CH2:17][OH:18])=[C:15]([CH3:19])[N:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]1[C:16]([CH:17]=[O:18])=[C:15]([CH3:19])[N:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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 1 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 3,5-dimethyl-1-pyridin-2-yl-1H-pyrazole-4-carbaldehyde as a yellow solid (0.358 g, 97%). MS (m/z): 202 (M+1).

Workup

extractionAdd saturated aqueous sodium bicarbonate and extract the aqueous 3 times with DCM, dry organic solution
filtrationthen filter
concentrationconcentrate
customPurify
washeluting with 20:80 hexanes

Sources & evidence

ORD record: ord-f0f9a6da82894277a75dad8b8186f9d0
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910588B2

Reaction notes

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