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

HRID 220471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220471
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

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66601738(3,5-dimethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol

Produkt 1

HCID 220544033,5-dimethyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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]+.

Aufarbeitung

  1. extractionAdd saturated aqueous sodium bicarbonate and extract the aqueous 3 times with DCM, dry organic solution
  2. filtrationthen filter
  3. concentrationconcentrate
  4. customPurify
  5. washeluting with 20:80 hexanes
  6. customethyl acetate to give the title

Quellen und Nachweise

ORD-Eintrag
ord-337e85ecf7d04a3baca30cb95638472d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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