2-Bromopyridine → Methyl 3-(pyridin-2-yl)benzoate

HRID 2201988Notes

Reaction equation

HRID 2201988 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][CH:18]=[CH:17][N: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:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 3364101Methyl 3-(pyridin-2-yl)benzoateYield 98.2%

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 (500 mg, 2.78 mmol), 2-bromopyridine (399 mg, 2.53 mmol), K2CO3 (1.0 g, 7.6 mmol) and Pd(dppf)Cl2 (20 mg) in a mixture solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 min under microwave heating. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by column chromatography to give the desired product (530 mg, Yield: 90%) and this was used directly in the next step. LCMS (m/z): 214.1.

Workup

  1. temperatureheating
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2539d5fef004495c97e3e2dfd6c2e126
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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