Potassium Carbonate → Ethyl 5'-chloro-2'-(1-((4'-chloro-[1,1'-biphenyl]-4-yl)amino)ethyl)-[1,1'-biphenyl]-4-carboxylate

HRID 2167143Notes

Reaction equation

HRID 2167143 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH3:10].[CH2:25]([O:27][C:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29])[CH3:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([CH:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH3:10])=[C:2]([C:33]2[CH:34]=[CH:35][C:30]([C:28]([O:27][CH2:25][CH3:26])=[O:29])=[CH:31][CH:32]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 71059978N-(1-(2-bromo-4-chlorophenyl)ethyl)-4'-chloro-[1,1'-biphenyl]-4-amine

Product 1

HCID 71059921Ethyl 5'-chloro-2'-(1-((4'-chloro-[1,1'-biphenyl]-4-yl)amino)ethyl)-[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(1-(2-bromo-4-chlorophenyl)ethyl)-4′-chloro-[1,1′-biphenyl]-4-amine (129 mg, 0.31 mmol), 4-(ethoxycarbonyl)phenylboronic acid (89 mg, 0.46 mmol), Pd(dppf) Cl2 (34 mg, 0.05 mmol), and K2CO3 (106 mg, 0.76 mmol) in wet DMF (3 mL) was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature and filtered. The filtrate was diluted with EtOAc, washed with water for and saturated aqueous NaHCO3, dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with water for and saturated aqueous NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-c4e8c2301a434abc8f897a81e94ed625
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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