Cesium carbonate → Methyl 3-(4-pyridyl)benzoate

HRID 2247418Notes

Reaction equation

HRID 2247418 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][C:4]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 5152687Methyl 3-(4-pyridyl)benzoateYield 68.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

1.121 g of 4-pyridylboronic acid, 2.35 g of methyl 3-bromobenzoate, 7.5 g of cesium carbonate and 530 mg of tetrakistriphenyl phosphine palladium were dissolved in 40 ml of N,N-dimethylformamide, and the mixture was stirred at 120° C. overnight in a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column, to give 1.325 g of the title compound in the 4:3 hexane-ethyl acetate fraction.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed
  4. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-7c9137528488494aa53e134b1e04d2e3
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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