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

HRID 1007678

反応式

HRID 1007678 の反応式
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]

参加物

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22598983Methyl 1-methyl-1H-indazole-6-carboxylate

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-34459832aea14c8bad9c092a8e89db1c
出典データセット
uspto-grants-2004_09
特許番号
US06794518B1

関連ノート

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