(2-Methyl-allyl)-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-trifluoromethyl-phenyl)-amine → Isobutyl-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-trifluoromethyl-phenyl)-amine

HRID 2427884Notes

Reaction equation

HRID 2427884 reaction equation
[CH3:1][C:2](=[CH2:32])[CH2:3][N:4]([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:16]=1)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1>CO.[Pd]>[CH2:3]([N:4]([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=2)[N:16]=1)[C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:10]=1)[CH:2]([CH3:32])[CH3:1]

Participants

4

Reactant 1

HCID 59161729(2-Methyl-allyl)-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-trifluoromethyl-phenyl)-amine

Product 1

HCID 59161710Isobutyl-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-trifluoromethyl-phenyl)-amineYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2-methyl-allyl)-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-trifluoromethyl-phenyl)-amine (270 mg, 0.6 mmol), Pd/C (10%, 30 mg) in methanol (30 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 (250 mg, 92%). 1H NMR (300 MHz, CDCl3) δ 8.12 (d, J=7.91 Hz, 2H), 7.70 (d, J=8.29 Hz, 2H), 7.58-7.66 (m, 2H), 7.38 (d, J=8.29 Hz, 2H), 7.06 (s, 1H), 6.45 (s, 1H), 3.95 (d, J=7.16 Hz, 2H), 2.25 (s, 3H), 2.10-2.22 (m, 1H), 0.98 (d, J=6.78 Hz, 6H). MS m/e 453.3 (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-fe883ff1839e415c853fff9c85d0b79a
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

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