Ethyl Acetate → HCID 21180499, compound

HRID 1386957Notes

Reaction equation

HRID 1386957 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][CH:11]=[C:12](I)[N:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)#[N:16].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]([C:21]3[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=3)[C:15]#[N:16])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 178477984HCID 178477984, compound

Product 1

HCID 21180499HCID 21180499, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-(3,4-dichloro-phenyl)-4-iodo-1H-imidazole (1.69 g, 5 mmol) and palladium tetrakis(triphenylphosphine) (0.29 g, 0.25 mmol) in toluene (25 ml) was stirred at r.t. for 15 min. 3-cyanophenylboronic acid (0.74 g, 5 mmol) and 2M K2CO3 solution (5 ml) was then added and the resulting mixture refluxed for 24 h. EtOAc (200 ml) was added and the organic phase was dried (Na2SO4), solvent eaporated and the residue chromatographed over SiO2 with EtOAc-hexane=1:1 to give 3-[2-(3,4-dichloro-phenyl)-3H-imidazol-4-yl]-benzonitrile (0.14 g, 9%) as a colorless mass. MS: m/e=313 (M+).

Workup

  1. temperaturethe resulting mixture refluxed for 24 h
  2. dry with materialthe organic phase was dried (Na2SO4), solvent eaporated
  3. customthe residue chromatographed over SiO2 with EtOAc-hexane=1:1

Sources & evidence

ORD record
ord-54ff03ea805a4652bb7edc75284b3f87
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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