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

HRID 550278

Reaction equation

HRID 550278 reaction equation
[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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8a561a309e804742b7f9745f230d0155
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Linked notes

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