2-[2-(4-Fluoro-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pent-4-enoic acid methyl ester → 2-[2-(4-Fluoro-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pentanoic acid methyl ester

HRID 2427874Notes

Reaction equation

HRID 2427874 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:12]=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:10]=1)[CH2:5][C:6]([CH3:8])=[CH2:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:32])[CH:4]([C:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=2)[N:12]=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 591617282-[2-(4-Fluoro-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pent-4-enoic acid methyl ester

Product 1

HCID 591617082-[2-(4-Fluoro-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pentanoic acid methyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-[2-(4-fluoro-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pent-4-enoic acid methyl ester (80 mg, 0.18 mmol), Pd/C (10%, 10 mg) in methanol (10 mL) was hydrogenated for 4 h. The mixture was filtered through Celite, washed with methanol, and evaporated. The residue was dissolved in CH2Cl2, filtered and evaporated to give the product as a colorless oil (80 mg, 100%). 1H NMR (300 MHz, CDCl3) δ 8.23 (d, J=8.29 Hz, 2H), 8.08-8.18 (m, 2H), 7.75 (d, J=8.29 Hz, 2H), 7.66 (d, J=1.88 Hz, 2H), 7.13-7.24 (m, 2H), 3.80 (t, J=7.72 Hz, 1H), 3.72 (s, 3H), 2.09 (dt, J=7.72, 13.56 Hz, 1H), 1.75 (dt, J=7.06, 13.75 Hz, 1H), 1.54 (dt, J=6.73, 13.28 Hz, 1H), 1.46-1.48 (m, 0H), 0.96 (d, J=6.40 Hz, 6H). MS m/e 446.3 (M+H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with methanol
  3. customevaporated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-47fdb5a14dd84239b14beddc9655a4dd
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

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