Potassium Carbonate → N-(2-bromo-4-(trifluoromethyl)benzyl)-2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

HRID 2167127Notes

Reaction equation

HRID 2167127 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12]Br.[Cl:14][C:15]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[CH3:29].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][NH:21][C:19]1[CH:18]=[CH:17][C:16]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[CH3:29])=[C:15]([Cl:14])[CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 149499362-Bromo-1-(bromomethyl)-4-(trifluoromethyl)benzeneHCID 866742052,4'-Dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

Product 1

HCID 86674206N-(2-bromo-4-(trifluoromethyl)benzyl)-2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-1-(bromomethyl)-4-(trifluoromethyl)benzene (2.0 g, 6.3 mmol), 2,4′-dichloro-2′-methyl-[1,1′-biphenyl]-4-amine (1.7 g, 6.9 mmol), and K2CO3 (1.3 g, 9.4 mmol) were diluted with DMF (20 mL) and heated to 80° C. After 3 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Sources & evidence

ORD record
ord-19d05245a77e4062a4f4bcf5483b2ec3
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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