(4-Methoxy-benzyl)-[4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]amine → 4-Trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine

HRID 1191207Notes

Reaction equation

HRID 1191207 reaction equation
COC1C=CC(C[NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[N:10]=2)=CC=1>CO.[Pd]>[F:18][C:15]([F:16])([F:17])[C:13]1[CH:12]=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:26])([F:28])[F:27])[N:10]=[C:9]([NH2:8])[CH:14]=1

Participants

4

Reactant 1

HCID 86657408(4-Methoxy-benzyl)-[4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]amine

Product 1

HCID 866574094-Trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (4-methoxy-benzyl)-[4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]amine (1.00 g, 2.34 mmol, prepared as described in STEP B above) in MeOH (20 mL) was added, the flask was flushed well with Ar, Pd/C (500 mg, 0.235 mmol, 5% on carbon) was added, and the flask was flushed with Ar and fitted with an H2 balloon. The resulting mixture stirred at room temperature for 4 h. The balloon was removed, the flask was flushed again with Ar, the mixture was filtered through diatomaceous earth, and the filter cake was washed well with MeOH. The filtrate was concentrated in vacuo to yield 4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-ylamine as a tan solid. 1H-NMR (400 MHz, CDCl3) δ: 7.81 (d, J=7.6 Hz, 1H), 7.64-7.76 (m, 2H), 7.59 (d, J=7.1 Hz, 1H), 7.25 (s, 1H), 6.79 (s, 1H), 3.22 (br. s., 4H).

Workup

  1. additionwas added
  2. customthe flask was flushed with Ar
  3. customfitted with an H2 balloon
  4. customThe balloon was removed
  5. customthe flask was flushed again with Ar
  6. filtrationthe mixture was filtered through diatomaceous earth
  7. washthe filter cake was washed well with MeOH
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-003e866901cc4157945e10270320e224
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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