Sodium Carbonate → HCID 18399500, compound

HRID 1019041Notes

Reaction equation

HRID 1019041 reaction equation
[N:1]1([CH2:6][CH:7]=[CH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11](OS(C(F)(F)F)(=O)=O)[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>C1(C)C=CC=CC=1.[Pd].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.C(O)C>[N:1]1([CH2:6]/[CH:7]=[CH:8]/[C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([C:31]3[CH:30]=[CH:29][C:28]([F:27])=[CH:33][C:32]=3[F:34])[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343342,4-Difluorophenylboronic acidHCID 53695128HCID 53695128, compound

Product 1

HCID 18399500HCID 18399500, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(trifluoromethylsulphonyloxy)benzoate (1.17 g; 3 mmol), 2,4-difluorophenylboronic acid (0.52 g; 3.3 mmol), tetrakis(triphenylphosphine) palladium (0.14 g; 0.12 mmol), 2M aqueous sodium carbonate solution (4.5 ml), lithium chloride (0.25 g; 6 mmol) and ethanol (13 ml) in toluene (120 ml) was refluxed, under an argon atmosphere, for 8 hours. The mixture was extracted with ethyl acetate and purified by flash chromatography eluting with isopropanol/dichloromethane (3/97) to give methyl 4-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(2,4-difluorophenyl)benzoate as a mixture of E and Z isomers.

Workup

  1. temperaturewas refluxed, under an argon atmosphere, for 8 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. custompurified by flash chromatography
  4. washeluting with isopropanol/dichloromethane (3/97)

Sources & evidence

ORD record
ord-f8bb685951194b1fb5ac59eee92a2e7d
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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