Methyl iodide → Methyl 2-methyl-2H-indazole-3-carboxylate

HRID 1372738

반응식

HRID 1372738 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.[H-].[Na+].[CH3:16]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:16][N:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[C:4]2[C:9]([CH:8]=[CH:7][CH:6]=[CH:5]2)=[N:1]1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 657476methyl 1H-indazole-3-carboxylate

생성물 1

HCID 11658425Methyl 2-methyl-2H-indazole-3-carboxylate수율 40.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Methyl indazole-3-carboxylate (3.71 g, 21.1 mmol) was dissolved in DMF (40 ml). To the resulting solution was added sodium hydride (60% in oil, 1.01 g, 25.3 mmol) in portions under stirring at 0° C. The reaction mixture was stirred at the same temperature for 30 minutes. Methyl iodide (1.57 ml, 25.3 mmol) was added to the mixture. The resulting mixture was stirred at the same temperature for 30 minutes. A saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (3:1, v/v) eluate fractions, methyl 2-methylindazole-3-carboxylate (1.62 g, 26%) was obtained as a pale yellow solid.

후처리

  1. stirringThe reaction mixture was stirred at the same temperature for 30 minutes
  2. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (3:1

출처 및 근거

ORD 기록
ord-f95a75addd494d208704cd6c559d5320
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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