Water → Ethyl 4-(hydroxymethyl)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylate

HRID 1639742Notes

Reaction equation

HRID 1639742 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1[O-])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[C:29]([O:34][CH2:35][CH3:36])(=[O:33])[C:30]#[C:31][CH3:32].O>CN(C)C=O>[OH:22][CH2:21][C:17]1[C:16]2[N:15]([N:14]=[C:31]([CH3:32])[C:30]=2[C:29]([O:34][CH2:35][CH3:36])=[O:33])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 866419191-Amino-3-(hydroxymethyl)pyridinium 2,4-dinitrobenzenolate

Product 1

HCID 59334472Ethyl 4-(hydroxymethyl)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylateYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-amino-3-(hydroxymethyl)pyridinium 2,4-dinitrobenzenolate (200 g, 0.650 mol) in dimethylformamide (1.3 L) was added potassium carbonate (224 g, 1.62 mol). To the mixture was added ethyl 2-butynoate (72.8 g, 0.650 mol) at room temperature, and the mixture was stirred for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (41.0 g, yield 27%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-a32c1ccb09454914aa1038c13b375251
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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