(4-Aminophenoxy)benzene → HCID 63587641, compound

HRID 876184Notes

Reaction equation

HRID 876184 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[O:9]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O.C1(C)C=CC=CC=1>[Cl:8][C:4]1[N:3]=[C:2]([NH:20][C:19]2[CH:18]=[CH:17][C:16]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:22][CH:21]=2)[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 8764(4-Aminophenoxy)benzeneHCID 11430Potassium CarbonateHCID 169892,6-DichloropyridineHCID 634876Binap, (A+-)-

Product 1

HCID 63587641HCID 63587641, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 mg of 2,6-dichloropyridine, 150 mg of 4-phenoxyaniline, 329 mg of K2CO3, 3 mg of Pd(OAc)2 and 9 mg of BINAP were charged into a microwave vial and 2.5 mL of dry toluene were added. The mixture obtained was treated in the vial analogously to the method as set out in Example 16a. For flash chromatography a solvent mixture of EtOAc:PE=1:10 was used. 6-Chloro-N-(4-phenoxyphenyl)pyridin-2-amine was obtained in the form of yellow crystals.

Workup

  1. additionwere added
  2. customThe mixture obtained
  3. additionwas treated in the vial analogously to the method

Sources & evidence

ORD record
ord-33a28d60743c47b4ab1aa89b836fd422
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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