Water → methyl 6-(1H-pyrazol-1-yl)nicotinate

HRID 735743

반응식

HRID 735743 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=C1.[H-].[Na+].Cl[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1.O.C[N:21](C=O)C>>[N:1]1([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=2)[CH:5]=[CH:4][CH:3]=[N:21]1

참가 물질

6

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 8027PyrroleHCID 24758Sodium hydrideHCID 254249Methyl 6-chloropyridine-3-carboxylate

생성물 1

HCID 3741563methyl 6-(1H-pyrazol-1-yl)nicotinate수율 64%

실험 절차

To a suspension of pyrrole (0.356 g, 5.23 mmol) in DMF (20 ml) was added sodium hydride (60% in oil, 0.233 g, 5.81 mmol). After stirring for 5 hrs., methyl 6-chloronicotinate (1.00 g, 5.81 mmol) was added, and the mixture was further stirred for 27 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried (over anhydrous MgSO4). After concentration under reduced pressure, the precipitated solid was collected by filtration and washed with hexane to give the title compound (0.683 g, 64%) as a colorless powder.

후처리

  1. stirringthe mixture was further stirred for 27 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried (over anhydrous MgSO4)
  5. concentrationAfter concentration under reduced pressure
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with hexane

출처 및 근거

ORD 기록
ord-a6d3df6cf14a42c886b1a8817231dd66
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592453B2

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