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

HRID 2167137Notes

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]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=1[CH3:32].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]([C:28]([F:29])([F:30])[F:31])=[CH:24][C:23]=2[CH3:32])=[C:15]([Cl:14])[CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Bromo-1-(bromomethyl)-4-(trifluoromethyl)benzene, prepared as described in Example 1 (2.5 g, 7.9 mmol), 2-chloro-2′-methyl-4′-(trifluoromethyl)-[1,1′-biphenyl]-4-amine, prepared as described in Example 2 (2.5 g, 8.7 mmol), and K2CO3 (1.6 g, 11.8 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

customprepared
washwashed with water and brine
dry with materialdried (Na2SO4)
customdry

Sources & evidence

ORD record: ord-d80474520ec14f16aa134c91f78ff267
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045389B2

Reaction notes

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