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

HRID 2389929Notes

Reaction equation

HRID 2389929 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][C:22]([CH3:24])=[CH:23][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[C:31]([O:37][CH2:38][CH3:39])(=[O:36])[C:32]#[C:33][CH2:34][CH3:35]>CN(C)C=O.O>[CH2:34]([C:33]1[C:32]([C:31]([O:37][CH2:38][CH3:39])=[O:36])=[C:16]2[C:17]3[CH:23]=[C:22]([CH3:24])[O:21][C:18]=3[CH:19]=[CH:20][N:15]2[N:14]=1)[CH3:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 99169Ethyl pent-2-yn-1-oateHCID 866386675-Amino-2-methylfuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

Product 1

HCID 59179437Ethyl 2-ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 38.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-2-methylfuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (1.44 g, 4.33 mmol), potassium carbonate (838 mg, 6.06 mmol) and ethyl 2-pentynoate (628 μL, 4.76 mmol) in dimethylformamide (20 mL) was stirred at room temperature for 14 hr. The reaction solution was diluted with water, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (451 mg, yield 38%).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)

Sources & evidence

ORD record
ord-54a79e1856c544d8b15f19189ea477a7
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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