Dimethylformamide dimethyl acetal → (2E)-3-(dimethylamino)-1-[2-(4-fluorophenyl)-6-(trifluoromethyl)-pyrazolo[1,5-a]pyridin-3-yl]-2-propen-1-one

HRID 2214945Notes

Reaction equation

HRID 2214945 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]>>[CH3:26][N:27]([CH3:29])/[CH:28]=[CH:22]/[C:21]([C:20]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:9][N:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=12)=[O:23]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 22174840HCID 22174840, compound

Product 1

HCID 11501715(2E)-3-(dimethylamino)-1-[2-(4-fluorophenyl)-6-(trifluoromethyl)-pyrazolo[1,5-a]pyridin-3-yl]-2-propen-1-one

Procedure

A mixture of 1-[2-(4-Fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone (11.85 g), 36.77 mmol) and N,N-dimethylformamide dimethyl acetal (100 mL) was stirred at reflux for 17 hours. 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 (73qb). 1H NMR (DMSO-d6): δ 9.44 (s, 1H), 8.22 (d, 1H, J=9.4Hz), 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 hours
  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-9c4850fe57df4ff18902c55bc8192473
Source dataset
uspto-grants-2006_09
Patent number
US07109209B2

Reaction notes

Loading…