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

HRID 405235Notes

Reaction equation

HRID 405235 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.[F: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]([F:24])=[CH:26][CH:27]=2)=[CH:36][CH:35]=1)[CH3:15]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 94624'-Fluoro(1,1'-biphenyl)-4-amineHCID 31297Methanesulfonyl chlorideHCID 574450731-(2-Bromo-4-chlorophenyl)ethanol

Product 1

HCID 71060075N-(1-(2-bromo-4-chlorophenyl)ethyl)-4'-fluoro-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat methanesulfonyl chloride (0.18 mL, 2.4 mmol) was added to a 0° C., DCM solution (20 mL) of 1-(2-bromo-4-chlorophenyl)ethanol (558 mg, 2.4 mmol) and Et3N (0.36 mL, 2.6 mmol) and the resulting mixture was allowed to warm to room temperature gradually. After 30 min Et3N (0.36 mL, 2.6 mmol) and 4′-fluoro-[1,1′-biphenyl]-4-amine (444 g, 2.4 mmol) were added sequentially and 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-caeff1b21d554846b9dfa00a271a2c41
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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