Dimethylformamide dimethyl acetal → 2-(4-Fluorophenyl)-3-(3-(dimethylamino)-2-propenoyl)-6-trifluoromethylpyrazolo[1,5-a]pyridine

HRID 1374719Notes

Reaction equation

HRID 1374719 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][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:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:20]([C:21](=[O:23])[CH:22]=[CH:26][N:27]([CH3:29])[CH3:28])=[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:6][CH:7]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 22174840HCID 22174840, compound

Product 1

HCID 694231242-(4-Fluorophenyl)-3-(3-(dimethylamino)-2-propenoyl)-6-trifluoromethylpyrazolo[1,5-a]pyridine

Procedure

A mixture of 2-(4-fluorophenyl)-3-acetyl-6-trifluoromethylpyrazolo[1,5-a]pyridine (11.85 g, 36.77 mmol) and N,N-dimethylformamide dimethyl acetal (100 mL) was stirred at reflux for 17 h. The mixture was cooled to room temperature and then to 0° C. The resulting orange precipitate was collected by filtration, washed with cold hexanes, and dried under vacuum to afford the title compound as an orange solid, 10.17 g (73%). 1H NMR (d6-DMSO) δ 9.44 (s, 1H), 8.22 (d, 1H, J=9.4 Hz), 7.75 (m, 2H), 7.65 (d, 1H, J=9.5 Hz), 7.56 (d, 1H, J=12.4 Hz), 7.35 (m, 2H), 5.05 (d, 1H, J=12.3 Hz), 3.04 (s, 3H), 2.56 (s, 3H). MS (+ve ion electrospray) 377 (80), (M+).

Workup

  1. temperatureat reflux for 17 h
  2. customto 0° C
  3. filtrationThe resulting orange precipitate was collected by filtration
  4. washwashed with cold hexanes
  5. customdried under vacuum

Sources & evidence

ORD record
ord-090a947b32954121adbce7aec59e87a6
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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