Water → HCID 86674210, compound

HRID 2167133Notes

Reaction equation

HRID 2167133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1I)[NH2:5].[Cl:10][C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.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:1][C:2]1[CH:3]=[C:4]([NH2:5])[CH:6]=[CH:7][C:8]=1[C:12]1[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=1[Cl:10]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2829263-Chloro-4-iodoanilineHCID 2783251[2-Chloro-4-(trifluoromethyl)phenyl]boronic acid

Product 1

HCID 86674210HCID 86674210, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Chloro-4-iodoaniline (3.0 g, 11.8 mmol), (2-chloro-4-(trifluoromethyl)phenyl)boronic acid (3.2 g, 14.2 mmol), Pd(dppf)Cl2 (969 mg, 1.2 mmol), and K2CO3 (3.3 g, 23.7 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Sources & evidence

ORD record
ord-3ec787aca20f4cc291ef972bfad92f7d
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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