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

HRID 1507035Notes

Reaction equation

HRID 1507035 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.O.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]>[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 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 3364101Methyl 3-(pyridin-2-yl)benzoateYield 74%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution (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 of dioxane (10 mL) and water (2.5 mL) was heated under microwave conditions at 120° C. for 0.5 h. The reaction mixture was filtered, concentrated, and the crude product was purified by column chromatography eluting with petroleum ether/ethyl acetate (5:1). (400 mg, yield 74%) MS (ESI+) e/z: 214.1 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe crude product was purified by column chromatography
  4. washeluting with petroleum ether/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-0b4e1e0d49e1428c9bf921991d0bb71f
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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