Sulfuric Acid → 2-(3-Methoxy-4-pyridin-2-ylphenyl)pyrazolo[1,5-a]pyridine

HRID 2213102Notes

Reaction equation

HRID 2213102 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:23](C(OCC)=O)=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.S(=O)(=O)(O)O>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[CH:23]=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21956522HCID 21956522, compound

Product 1

HCID 103801282-(3-Methoxy-4-pyridin-2-ylphenyl)pyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-(3-methoxy-4-pyridin-2-ylphenyl)pyrazolo[1,5-a]pyridin-3-carboxylate (25 mg, 0.013 mmol) was treated with 40% sulfuric acid (1 mL), and the reaction mixture was heated to 100° C. for 12 h. The cooled reaction mixture was diluted with a solution of saturated aqueous sodium carbonate (25 mL), and the product was extracted into CH2Cl2 (3×20 mL), dried (MgSO4) and concentrated to afford 2-(3-methoxy-4-pyridin-2-ylphenyl)pyrazolo[1,5-a]pyridine.

Workup

  1. customThe cooled reaction mixture
  2. extractionthe product was extracted into CH2Cl2 (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe32b9dc06a34722be237a023721bf3c
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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