HCID 59161724, compound → HCID 59161732, compound

HRID 2427868Notes

Reaction equation

HRID 2427868 reaction equation
[CH3:1][O:2][C:3](=[O:35])[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]([C:31]([F:34])([F:33])[F:32])=[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:35])[CH:4]([C:9]1[CH:10]=[C:11]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=2)[N:12]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 59161724HCID 59161724, compound

Product 1

HCID 59161732HCID 59161732, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-[2,6-bis-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pent-4-enoic acid methyl ester (280 mg, 0.57 mmol), Pd/C (10%, 30 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 white solid (260 mg, 92%). 1H NMR (300 MHz, CDCl3) δ 8.24 (d, J=8.29 Hz, 4H), 7.76 (d, J=8.29 Hz, 4H), 7.73 (s, 2H), 3.82 (t, J=7.72 Hz, 1H), 3.72 (s, 3H), 2.11 (dt, J=7.72, 13.94 Hz, 1H), 1.76 (dt, J=6.92, 13.66 Hz, 1H), 1.49-1.62 (m, 1H), 0.97 (d, J=6.40 Hz, 6H). MS m/e 496.2 (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-e18f6a8f94ec4ea8aeeaf06104ec1052
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

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