Potassium Carbonate → Methyl 3-(3-pyridinyl)benzoate

HRID 2201996Notes

Reaction equation

HRID 2201996 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:16]=[N:17][CH:18]=[CH:19][CH:20]=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:17]1[CH:18]=[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]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoateYield 90%

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), 3-bromopyridine (479 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 minutes with microwave heating under N2. The catalyst was then filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the desired product and used directly in the next step. (630 mg Yield 90%).

Workup

  1. temperaturewith microwave heating under N2
  2. filtrationThe catalyst was then filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-a4e7326ebdf64e65bdd023710d273d12
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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