Potassium Carbonate → Methyl-3-bromo-5-(3-pyridyl)benzoate

HRID 431877Notes

Reaction equation

HRID 431877 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[C:6]([Br:11])[CH:5]=1.B1([C:19]2[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=2)OCCCO1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:7]=[C:6]([Br:11])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 21942573Methyl 3-bromo-5-iodobenzoate

Product 1

HCID 21942604Methyl-3-bromo-5-(3-pyridyl)benzoateYield 67.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of Methyl-3-bromo-5-iodobenzoate (2.00 g, 5.87 mmol) in toluene (50 ml) added Pyridine-3-boronic acid-1,3-propanediol ester (1.24 g, 7.63 mmol), potassium carbonate (8.11 g, 58.7 mmol) and tetrakis(triphenylphoshine)palladium (0) (0.34, 0.29 mmol), sequentially. The resulting brownish yellow reaction mixture was heated at 80° C. under argon for 10 h. The reaction mixture was cooled to room temperature, filtered through a pad of celite and concentrated in-vacuo. The residue was purified on silica gel using 3% methanol in dichloromethane to isolate Methyl-3-bromo-5-(3-pyridyl)benzoate (1.16 g, 67%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite and
  3. concentrationconcentrated in-vacuo
  4. customThe residue was purified on silica gel using 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-ed585bb9e9d04a2598d44a04ce25484b
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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