Dimethylformamide → methyl 3-formyl-1-methyl-1H-indazole-6-carboxylate

HRID 1007678

반응식

HRID 1007678 반응식
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=2)[CH:9]=[N:8]1.[OH-].[Na+].CN([CH:25]=[O:26])C>>[CH:25]([C:9]1[C:10]2[C:15](=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)[N:7]([CH3:6])[N:8]=1)=[O:26]

참가 물질

5

반응물 4

HCID 6228Dimethylformamide2회HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22598983Methyl 1-methyl-1H-indazole-6-carboxylate

생성물 1

HCID 22598959methyl 3-formyl-1-methyl-1H-indazole-6-carboxylate

실험 절차

In a dry flask under nitrogen is added dry DMF (1.6 mL) and the solution cooled to −5C in an ice/ethanol bath. Phosphorous oxychloride (530 uL, 5.7 mmol) is added via syringe and the solution is allowed to stir for 30 minutes in the bath. Methyl 1-methyl-1H-indazole-6-carboxylate, (500 mg, 2.84 mmol, prepared as in Jadhav et al, U.S. Pat. No. 5,760,028) dissolved in DMF (3 mL) is added slowly to the cold solution. The reaction is then warmed to 35C, stirred for four hours, and then poured onto crushed ice. The resulting slurry is neutralized with 1N NaOH to pH=7, heated rapidly to boiling for 1 minute, cooled quickly to room temperature, and the solution extracted with ethyl acetate. The combined organics are washed with water and brine, dried, filtered and concentrated. The resulting oil is purified by flash chromatography to afford the product.

후처리

  1. temperaturethe solution cooled to −5C in an ice/ethanol bath
  2. additionis added slowly to the cold solution
  3. stirringstirred for four hours
  4. additionpoured
  5. customonto crushed ice
  6. temperatureheated rapidly
  7. waitto boiling for 1 minute
  8. extractionthe solution extracted with ethyl acetate
  9. washThe combined organics are washed with water and brine
  10. customdried
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe resulting oil is purified by flash chromatography
  14. customto afford the product

출처 및 근거

ORD 기록
ord-34459832aea14c8bad9c092a8e89db1c
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794518B1

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