(2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]acrylamide → N-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]propanamide

HRID 1994152Notes

Reaction equation

HRID 1994152 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:25])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27]>CO.CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:25])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)=[CH:16][CH:17]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:27])[F:28]

Participants

5

Reactant 1

HCID 58674375(2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]acrylamide

Product 1

HCID 58674529N-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]propanamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]acrylamide (70 mg, 0.17 mmol) in MeOH (2 mL) and EtOAc (2 mL) was added Pd/C (10 wt %, 20 mg). The mixture was stirred under hydrogen (60 psi) for 18 h and then filtrated through Celite. The filtrate was concentrated and purified by column chromatography to give A-84 (28 mg, 41%). 1H NMR (300 MHz, CD3OD) δ: 8.35 (d, 2H), 8.03 (d, 1H), 7.70 (dd, 1H), 7.48 (d, 1H), 7.10-7.24 (m, 6H), 3.96 (s, 2H), 2.97 (dd, 2H), and 2.65 (dd, 2H). LCMS: (FA) ES+ 419.2 (M+1), ES− 417.2 (M−1).

Workup

  1. filtrationfiltrated through Celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography
  4. customto give A-84 (28 mg, 41%)

Sources & evidence

ORD record
ord-cd32321d0ac349feb979f97ea70bf85e
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

Loading…