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

HRID 1374716Notes

Reaction equation

HRID 1374716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=[O:19])[CH3:18])=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=[O:19])[CH:18]=[CH:22][N:23]([CH3:25])[CH3:24])=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 179624172-(4-Fluorophenyl)-3-acetylpyrazolo[1,5-a]pyridine

Product 1

HCID 694242312-(4-Fluorophenyl)-3-(3-(dimethylamino)-2-propenoyl)pyrazolo[1,5-a]pyridine

Procedure

A mixture of 2-(4-fluorophenyl)-3-acetylpyrazolo[1,5-a]pyridine (1.0 g, 3.93 mmol) in N,N-dimethylformamide dimethyl acetal (10 mL) was stirred and heated at reflux for 17 h. The mixture was cooled to room temperature and the volatiles evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluded with 1% MeOH/CH2Cl2) to afford the title compound as an orange solid, 0.830 g (68%). 1H NMR (CDCl3) 88.50 (d, 1H, J=6.9 Hz), 8.39 (d, 1H, J=9.0 Hz), 7.83 (d, 2H, J=12.6 Hz), 7.73 (m, 2H), 7.39 (m, 1H), 7.20 (m, 2H), 6.93 (m, 1H), 5.13 (d, 1H, J=12.5 Hz), 3.10 (s. 3H), 2.56 (s, 3H). MS (+ve ion electrospray) 310 (90), (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 17 h
  3. customthe volatiles evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluded with 1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-994579a081c04b1e9c06e3558810f34e
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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