Dimethyl Sulfoxide → 5-Methyl-1-pyridin-2-yl-1H-pyrazole-4-carbaldehyde

HRID 604302

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve dimethyl sulfoxide (0.751 mL, 10.6 mmol) in DCM (20 mL) and cool to −78° C. Add oxalyl chloride (0.577 mL, 6.62 mmol) dropwise in DCM (8 mL) and stir for 15 min. Add (5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol (0.501 g, 2.65 mmol) in DCM (20 mL) dropwise and stir for 1 hr. at −78° C. Add triethylamine (1.85 mL, 13.2 mmol) and warm the mixture to room temperature for 1 hr. Dilute the mixture with saturated sodium bicarbonate and extract three times with DCM. Dry (sodium sulfate) the solution, filter and concentrate to give 5-methyl-1-pyridin-2-yl-1H-pyrazole-4-carbaldehyde as a white solid (0.496 g, 100%). MS (m/z): 188 (M+1).

Workup

customat −78° C
extractionextract three times with DCM
dry with materialDry (sodium sulfate) the solution
filtrationfilter
concentrationconcentrate

Sources & evidence

ORD record: ord-9d510d2d15f44be1a7e1c417e15ad2de
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910588B2

Linked notes

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