Potassium Carbonate → Ethyl furo[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

HRID 2389870Notes

Reaction equation

HRID 2389870 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1[O-])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]2[O:21][CH:22]=[CH:23][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]([O:34][CH2:35][CH3:36])(=[O:33])[C:31]#[CH:32]>CN(C)C=O.O>[C:31]1([C:30]([O:34][CH2:35][CH3:36])=[O:33])[CH:32]=[N:14][N:15]2[CH:20]=[CH:19][C:18]3[O:21][CH:22]=[CH:23][C:17]=3[C:16]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12182Ethyl propiolateHCID 866386655-Aminofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

Product 1

HCID 59179413Ethyl furo[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-aminofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (1.00 g, 3.14 mmol) and potassium carbonate (608 mg, 4.40 mmol) in dimethylformamide (20 mL) was added ethyl propiolate (350 μL, 3.45 mmol) under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction solution was diluted with water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→440/60) to give the title compound (451 mg, yield 62%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→440/60)

Sources & evidence

ORD record
ord-8258568fc6604c12887eec62deb7e523
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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