Acetic Anhydride → HCID 22174840, compound

HRID 1374718Notes

Reaction equation

HRID 1374718 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:20]=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].[OH-].[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:20]([C:21](=[O:23])[CH3:22])=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:18])([F:17])[F:19])=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 99217692-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)PYRAZOLO[1,5-A]PYRIDINE

Product 1

HCID 22174840HCID 22174840, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a mixture of 2-(4-fluorophenyl)-6-trifluoromethylpyrazolo[1,5-a]pyridine (10.30 g, 36.76 mmol) and acetic anhydride (100 mL) was added conc. sulfuric acid (10 drops) and the mixture was stirred and heated at reflux for 1 h. The reaction mixture was cooled to room temperature and poured into ice water (300 mL). 2N Aqueous sodium hydroxide solution was added to raise the pH of the solution to about 10 and the resulting orange precipitate was collected by filtration. The solid was washed with water, air-dried, and then dried under vacuum to afford the title compound as an orange solid, 11.87 g (quant.). 1H NMR (d6-DMSO) δ 9.58 (s, 1H), 8.41 (d, 1H, J=9.3 Hz), 7.89 (d, 1H, J=9.5 Hz), 7.74 (m, 2H), 7.39 (m, 2H), 2.22 (s, 3H). MS (+ve ion electrospray) 323 (70), (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. temperatureto raise the pH of the solution to about 10
  4. filtrationthe resulting orange precipitate was collected by filtration
  5. washThe solid was washed with water
  6. customair-dried
  7. customdried under vacuum

Sources & evidence

ORD record
ord-711bc372137144d68361e0bb56b930af
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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