Water → Ethyl pyrazolo(1,5-a)pyridine-3-carboxylate

HRID 1500753Notes

Reaction equation

HRID 1500753 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][CH3:3].[I-].[NH2:9][N+:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[N:9]1[N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=[C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7749Ethyl PropionateHCID 11430Potassium CarbonateHCID 2733704Pyridinium, 1-amino-, iodide (1:1)

Product 1

HCID 2795464Ethyl pyrazolo(1,5-a)pyridine-3-carboxylateYield 50.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl propionate (50.2 mL, 49.54 mmol) and 1-aminopyridinium iodide (10.0 g, 45 mmol) were added to a suspension of potassium carbonate (8.71 g, 63.02 mmol) in N,N′-dimethylformamide (100 mL) and the resulting mixture was stirred at room temperature for 2 h before being poured into 100 mL of water. Ethyl acetate was then added and the aqueous layer was separated and washed with ethyl acetate (×2). The combined organic layers were dried over magnesium sulphate, filtered and evaporated. The crude product was purified by flash chromatography (hexanes to 4:1 hexanes/ethyl acetate) to give the title compound (4.30 g, 50%) as an orange solid.

Workup

  1. customthe aqueous layer was separated
  2. washwashed with ethyl acetate (×2)
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (hexanes to 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-4595d3b4cce34da385b5d3d0168d3b06
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

Loading…