Water → 4'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amine

HRID 405228Notes

Reaction equation

HRID 405228 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([CH3:19])[CH:11]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)=[C:12]([CH3:19])[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 5017600(4-Chloro-2-methylphenyl)boronic acid

Product 1

HCID 672116234'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

4-iodoaniline (3.3 g, 15.0 mmol), (4-chloro-2-methylphenyl)boronic acid (3.3 g, 19.5 mmol), Pd(dppf)Cl2 (1.22 g, 1.5 mmol), and K2CO3 (4.1 g, 30 mmol) were dissolved in 1,4-dioxane (60 mL) and water (15 mL) and heated to 90° C. After 3 h the resulting mixture was diluted EtOAc and water and the layers were separated. The organic layer was dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. customEtOAc and water and the layers were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-68b862a9b07748e7a3e2226d2b47a193
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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