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

HRID 2252471

反応式

HRID 2252471 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 −5 C 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 35 C, 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 −5 C in an ice/ethanol bath
  2. additionis added slowly to the cold solution
  3. temperatureThe reaction is then warmed to 35 C
  4. stirringstirred for four hours
  5. additionpoured
  6. customonto crushed ice
  7. temperatureheated rapidly
  8. waitto boiling for 1 minute
  9. extractionthe solution extracted with ethyl acetate
  10. washThe combined organics are washed with water and brine
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe resulting oil is purified by flash chromatography
  15. customto afford the product

出典と根拠

ORDレコード
ord-1079432937ee4786a3e2ae42abeb65f2
出典データセット
uspto-grants-2008_01
特許番号
US07321045B2

関連ノート

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