Triethylamine → N-(1-(2-bromo-4-chlorophenyl)ethyl)-4'-chloro-[1,1'-biphenyl]-4-amine

HRID 2167142Notes

Reaction equation

HRID 2167142 reaction equation
CS(Cl)(=O)=O.[Br:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[CH:14](O)[CH3:15].CCN(CC)CC.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1>C(Cl)Cl>[Br:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[CH:14]([NH:37][C:34]1[CH:33]=[CH:32][C:31]([C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=2)=[CH:36][CH:35]=1)[CH3:15]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 86754-Amino-4'-chlorodiphenylHCID 31297Methanesulfonyl chlorideHCID 574450731-(2-Bromo-4-chlorophenyl)ethanol

Product 1

HCID 71059978N-(1-(2-bromo-4-chlorophenyl)ethyl)-4'-chloro-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat methanesulfonyl chloride (0.40 mL, 5.1 mmol) was added to a 0° C., DCM solution (20 mL) of 1-(2-bromo-4-chlorophenyl)ethanol (1.2 g, 5.1 mmol) and Et3N (0.78 mL, 5.6 mmol) and the resulting mixture was allowed to warm to room temperature gradually. After 30 min, Et3N (0.78 mL, 5.6 mmol) and 4′-chloro-[1,1′-biphenyl]-4-amine (1.0 g, 5.1 mmol) were added sequentially and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was concentrated and purified via column chromatography to yield the title compound.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated
  2. custompurified via column chromatography

Sources & evidence

ORD record
ord-16c3c402bbb24ee499685032c78d5707
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

Loading…