Potassium Carbonate → Ethyl 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

HRID 2389872Notes

Reaction equation

HRID 2389872 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][CH2:22][CH2:23][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][CH2:22][CH2:23][C:17]=3[C:16]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12182Ethyl propiolateHCID 866386665-Amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

Product 1

HCID 59179449Ethyl 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (8.00 g, 25.0 mmol) and potassium carbonate (4.84 g, 35.0 mmol) in dimethylformamide (100 mL) was added ethyl propiolate (2.80 mL, 27.6 mmol) under ice-cooling, and the mixture was stirred at room temperature for 20 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→40/60) to give the title compound (980 mg, yield 17%).

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→40/60)

Sources & evidence

ORD record
ord-acdc7c3ad3df4d24b063db7f37f453a6
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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