Potassium Carbonate → 2-Ethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

HRID 1802749Notes

Reaction equation

HRID 1802749 reaction equation
[I-].[NH2:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:17][C:18](=[O:23])[C:19]#[C:20][CH2:21][CH3:22])[CH3:16]>CN(C)C=O>[CH2:15]([O:17][C:18]([C:19]1[C:20]([CH2:21][CH3:22])=[N:2][N:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=12)=[O:23])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 99169Ethyl pent-2-yn-1-oateHCID 2733704Pyridinium, 1-amino-, iodide (1:1)

Product 1

HCID 137381512-Ethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl esterYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of amino-pyridinium iodide (22 g, 99 mmol) and anhydrous potassium carbonate (17.8 g, 128.7 mmol) in dimethylformamide (225 mL) was added ethyl-2-pentynoate (24.98 g, 198 mmol). The solution was stirred at room temperature for 24 h. The reaction mixture was poured into 1.2 L of ice water. The resulting light brown precipitate was collected by vacuum filtration and air-dried for 16 h to yield crude product (11.9 g, 55%), which was used without further purification.

Workup

  1. filtrationThe resulting light brown precipitate was collected by vacuum filtration
  2. customair-dried for 16 h

Sources & evidence

ORD record
ord-7800cdd767f24a2da8847c9987a2c542
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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