Sodium Carbonate → HCID 67505374, compound

HRID 1929827Notes

Reaction equation

HRID 1929827 reaction equation
Br[C:2]1[C:3]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:3]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 67504974HCID 67504974, compound

Product 1

HCID 67505374HCID 67505374, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

3-Bromo-5-methyl-2-phenoxy-pyridine (0.79 g, 3.0 mmol) was dissolved in toluene (5 mL). To this solution was added [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) dichloro-methane complex (120 mg), 4-chlorophenyl-boronic acid (0.7 g, 4.5 mmol), and 2 N sodium carbonate solution (4.7 mL). The whole mixture was heated with stirring at 90° C. for 18 h, cooled to room temperature and eluted with ethyl acetate over 10 g ChemElut (Varian). The solvent was evaporated and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient) to yield 0.61 g of the title compound as a yellowish oil, MS (ISP) 296.4 (M+H)+.

Workup

  1. temperatureThe whole mixture was heated
  2. temperaturecooled to room temperature
  3. washeluted with ethyl acetate over 10 g ChemElut (Varian)
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-513ddd7f879148c79b3d3d34227a6ff1
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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