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

HRID 2389873Notes

Reaction equation

HRID 2389873 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:36][CH2:37][CH3:38])(=[O:35])[C:31]#[C:32][CH2:33][CH3:34]>CN(C)C=O.O>[CH2:33]([C:32]1[C:31]([C:30]([O:36][CH2:37][CH3:38])=[O:35])=[C:16]2[C:17]3[CH2:23][CH2:22][O:21][C:18]=3[CH:19]=[CH:20][N:15]2[N:14]=1)[CH3:34]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 99169Ethyl pent-2-yn-1-oateHCID 866386665-Amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

Product 1

HCID 53310990Ethyl 2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 12.2%

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 2-pentynoate (3.63 mL, 27.5 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 (794 mg, yield 12%).

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-77e41a38727442d5b246fcbb81e7012c
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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