(E)-ethyl 2-methyl-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acrylate → ethyl 2-methyl-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propanoate

HRID 573841Notes

Reaction equation

HRID 573841 reaction equation
[CH3:1]/[C:2](=[CH:8]\[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4]>[Pd].C(OCC)(=O)C>[CH3:1][CH:2]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]=[CH:18][N:17]([C:20]3[CH:21]=[CH:22][C:23]([O:26][C:27]([F:29])([F:30])[F:28])=[CH:24][CH:25]=3)[N:16]=2)=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 1

HCID 90438205(E)-ethyl 2-methyl-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acrylate

Product 1

HCID 90405493ethyl 2-methyl-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propanoateYield 103.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A flask containing (E)-ethyl 2-methyl-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acrylate (C36) (0.96 g, 2.3 mmol) and palladium on carbon (10 wt %, 0.24 g, 0.23 mmol) in ethyl acetate (10 mL) was evacuated under vacuum, filled with nitrogen, evacuated under vacuum, and then placed under hydrogen by balloon (˜1 atm). After stirring at room temperature for 20 hours, the reaction was filtered through a pad of Celite® and concentrated to afford the title compound as a white solid (1.0 g, 100%): mp 73-75° C.; 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.14-8.07 (m, 2H), 7.86-7.76 (m, 2H), 7.39 (d, J=8.3 Hz, 2H), 7.29 (d, J=8.3 Hz, 2H), 4.10 (q, J=7.1 Hz, 2H), 3.22-2.99 (m, 1H), 2.75 (dq, J=13.3, 7.5 Hz, 2H), 1.24-1.15 (m, 6H); 19F NMR (376 MHz, CDCl3) δ −58.03; ESIMS m/z 420 ([M+H]+).

Workup

  1. customwas evacuated under vacuum
  2. additionfilled with nitrogen
  3. customevacuated under vacuum
  4. filtrationthe reaction was filtered through a pad of Celite®
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c442434dea3446082a65d2fdd136a03
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

Loading…