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

HRID 2201999Notes

Reaction equation

HRID 2201999 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-066b31a2310644c2a44bbf1659b8766f
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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