Dimethylformamide → HCID 22174842, compound

HRID 1797062Notes

Reaction equation

HRID 1797062 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:25]=[C:16]3[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][N:15]3[N:14]=2)=[CH:9][CH:8]=1.CN(C)[CH:28]=[O:29]>>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:25]([CH:28]=[O:29])=[C:16]3[CH:17]=[CH:18][C:19]([C:21]([F:23])([F:22])[F:24])=[CH:20][N:15]3[N:14]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 99217692-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)PYRAZOLO[1,5-A]PYRIDINE

Product 1

HCID 22174842HCID 22174842, compoundYield 94%

Procedure

To a cold (0° C.) solution of phosphorus oxychloride (8.0 mL, 86 mmol) in N,N-dimethylformamide (160 mL) was added 2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo-[1,5-a]pyridine (11.0 g, 39.3 mmol). The reaction mixture was stirred at room temperature for 72 hours, then quenched with ice water. The solid precipitate was collected on a filter to provide 2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (11.4 g, 94%) as a white solid. Rf 0.45 (4:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 10.15 (s, 1H), 8.92 (s, 1H), 8.53 (d, 1H), 7.80 (m, 2H), 7.70 (d, 1H), 7.27 (t, 2H); 19F NMR (CDCl3) δ −62.62, −110.62; MS m/z 307 (M−1).

Workup

  1. customquenched with ice water
  2. customThe solid precipitate was collected on
  3. filtrationa filter

Sources & evidence

ORD record
ord-6af9e99282f6482a98ab09012cb564af
Source dataset
uspto-grants-2006_04
Patent number
US07034030B2

Reaction notes

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