Methyl [3,5-bis(trifluoromethyl)benzyl]({2'-methoxy-4-(trifluoromethyl)-5'-[1-(trifluoromethyl)vinyl]biphenyl-2-yl}methyl)carbamate → Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-4-(trifluoromethyl)-5'-(2,2,2-trifluoro-1-methylethyl)biphenyl-2-yl]methyl}carbamate

HRID 217534Notes

Reaction equation

HRID 217534 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([C:29]([C:31]([F:34])([F:33])[F:32])=[CH2:30])[CH:26]=[CH:25][C:24]=1[O:35][CH3:36])[C:8](=[O:11])[O:9][CH3:10]>CO.[Pd]>[F:1][C:2]([F:44])([F:45])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:39]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH:29]([CH3:30])[C:31]([F:32])([F:33])[F:34])[CH:26]=[CH:25][C:24]=1[O:35][CH3:36])[C:8](=[O:11])[O:9][CH3:10]

Participants

4

Reactant 1

HCID 86615401Methyl [3,5-bis(trifluoromethyl)benzyl]({2'-methoxy-4-(trifluoromethyl)-5'-[1-(trifluoromethyl)vinyl]biphenyl-2-yl}methyl)carbamate

Product 1

HCID 11585537Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-4-(trifluoromethyl)-5'-(2,2,2-trifluoro-1-methylethyl)biphenyl-2-yl]methyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound from Step A (10 mg, 0.017 mmol) was hydrogenated at 1 atm in methanol using Pd/C as the catalyst. The solution was filtered through Celite then concentrated. The title compound was purified by preparative thin layer chromatography using 1:4 EtOAc:hexane.

Workup

  1. filtrationThe solution was filtered through Celite
  2. concentrationthen concentrated
  3. customThe title compound was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-e3ec55c6dcc94640b2fc43eec22762f0
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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