Potassium Carbonate → Ethyl 2-methylpyrazolo[1,5-a]pyridine-3-carboxylate

HRID 2282319Notes

Reaction equation

HRID 2282319 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+].[C:15]([O:20][CH2:21][CH3:22])(=[O:19])[C:16]#[C:17][CH3:18]>CN(C=O)C>[CH3:18][C:17]1[C:16]([C:15]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]2[N:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 2733704Pyridinium, 1-amino-, iodide (1:1)

Product 1

HCID 12872285Ethyl 2-methylpyrazolo[1,5-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-aminopyridinium iodide (19 g, 86 mmol) and potassium carbonate (12 g, 86 mmol) in DMF (100 mL) was added ethyl 2-butynoate (8.0 g, 71 mmol) and the reaction stirred overnight. The DMF was removed by rotary evaporation and the resulting solid was taken up in EtOAc (200 ml) and water (200 ml), partitioned and the aqueous phase extracted with 2×150 ml EtOAc. The combined organics were washed with brine, dried over MgSO4 and concentrated.

Workup

  1. customThe DMF was removed by rotary evaporation
  2. customwater (200 ml), partitioned
  3. extractionthe aqueous phase extracted with 2×150 ml EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c4af68093f2643df8d5da085bc594852
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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