Potassium Carbonate → Methyl 3-(4-pyridyl)benzoate

HRID 880256Notes

Reaction equation

HRID 880256 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].Br[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N:18]1[CH:19]=[CH:20][C:15]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 142684-BromopyridineHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 5152687Methyl 3-(4-pyridyl)benzoateYield 98.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (600 mg, 3.33 mmol), 4-bromopyridine (583.5 mg, 3.0 mmol), K2CO3 (1.2 g, 9.0 mmol) and Pd(dppf)Cl2 (50 mg) in a solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 min with microwave heating. The catalyst was filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the title product (630 mg Yield 90%).

Workup

  1. temperatureheating
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-0d5b609796d5498da36237ae9c0f9c11
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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