Acetic Acid → N-(2-bromo-4-(trifluoromethyl)benzyl)-4'-chloro-[1,1'-biphenyl]-4-amine

HRID 405162

Reaction equation

HRID 405162 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Br:15][C:16]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:17]=1[CH:18]=O.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1.CC(O)=O>CCOC(C)=O.ClCCCl>[Br:15][C:16]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH:41][C:38]1[CH:37]=[CH:36][C:35]([C:32]2[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=2)=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 86754-Amino-4'-chlorodiphenylHCID 30203732-Bromo-4-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 71059841N-(2-bromo-4-(trifluoromethyl)benzyl)-4'-chloro-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (1.4 g, 6.8 mmol) was added to a DCE solution (10 mL) of 2-bromo-4-(trifluoromethyl)benzaldehyde (860 mg, 3.4 mmol), 4′-chloro-[1,1′-biphenyl]-4-amine (761 mg, 3.7 mmol), and AcOH (0.78 mL, 13.6 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry-packed onto silica gel and purified via column chromatography

Sources & evidence

ORD record
ord-adcbe94aa6b841e3be59a4fac222ba32
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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