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

HRID 220479

반응식

HRID 220479 반응식
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]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66438330(5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol

생성물 1

HCID 210973525-Methyl-1-pyridin-2-yl-1H-pyrazole-4-carbaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 516892Sodium Bicarbonate용매

반응 조건

온도
-78 °C

실험 절차

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 one hr. at −78° C. Add triethylamine (1.85 mL, 13.2 mmol) and warm the mixture to room temperature for one hr. Dilute the mixture with saturated sodium bicarbonate and extract 3 times with DCM. Dry (sodium sulfate) the solution, filter and concentrate to give the title preparation as a white solid (0.496 g, 100%). MS (ES): m/z=188 [M+H]+.

후처리

  1. customat −78° C
  2. extractionextract 3 times with DCM
  3. dry with materialDry (sodium sulfate) the solution
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give the title

출처 및 근거

ORD 기록
ord-ed62302a164a4ba78d7e2b01acc774c4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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