Acetic Anhydride → HCID 17962425, compound

HRID 1374723Notes

Reaction equation

HRID 1374723 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[C:11]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[C:21](OC(=O)C)(=[O:23])[CH3:22]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:18]([C:21](=[O:23])[CH3:22])=[C:11]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 18376035HCID 18376035, compound

Product 1

HCID 17962425HCID 17962425, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
120 °C

Procedure

A solution of 2-(4-fluorophenyl)-6-cyanopyrazolo[1,5-a]pyridine (6.7 g, 11 mmol) and concentrated sulfuric acid (2 drops) in acetic anhydride (25 mL) was heated, and stirred, at 120° C. under N2 for 5 h. The solution was cooled to room temperature, diluted with ice water and basified to pH 11 using 2 N aqueous sodium hydroxide. The solution was extracted with chloroform (3×), and the combined organic extracts were dried and the solvent was evaporated in vacuo. Trituration with methanol afforded a light brown solid which was collected and dried to give the title compound, 1.6 g (84%). 1H NMR (d6-DMSO) δ 2.19 (s, 3H), 7.35 (t, 2H, J=8.0 Hz), 7.69 (dd, 2H, J=4.0, 8.0 Hz), 7.86 (dd, 1H, J=4.0, 16 Hz), 8.30 (d, 1H, J=12 Hz), 9.75 (s, 1H). MS (ES+) m/z 280 (M++H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe solution was extracted with chloroform (3×)
  3. customthe combined organic extracts were dried
  4. customthe solvent was evaporated in vacuo
  5. customTrituration with methanol afforded a light brown solid which
  6. customwas collected
  7. customdried

Sources & evidence

ORD record
ord-646d900f29124714acd37b18221622b7
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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