3-Bromopyridine → 3-(4-Pyridin-3-yl-phenyl)propionic acid ethyl ester

HRID 2218128Notes

Reaction equation

HRID 2218128 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([O:10][C:11]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)=[O:12])[CH3:9]>CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].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]>[CH2:8]([O:10][C:11](=[O:12])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH3:9]

Participants

7

Reactant 2

HCID 122863-BromopyridineHCID 38517004-(2-Ethoxycarbonylethyl)benzeneboronic acid

Product 1

HCID 693000763-(4-Pyridin-3-yl-phenyl)propionic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

1,1′-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.1 g, 0.1 mmol) was added to a stirred and degassed solution of 3-bromopyridine (1.5 ml, 15.6 mmol) and 4-[2-ethoxycarbonylethyl]phenylboronic acid (P20) (3.5 g, 15.8 mmol) in dimethyl formamide (30 mL) and 2N sodium carbonate solution in water (15 mL). The reaction mixture was stirred at 100° C. for 18 hours, then allowed to cool. The solution was filtered through celite, then ethyl acetate (100 mL) was added and the organic phase was washed three times with brine (100 mL). The organic layer was dried (anhydrous magnesium sulfate), concentrated and purified by chromatography on silica gel (30% v/v ethyl acetate in petroleum ether) to afford the title compound as an oil.

Workup

  1. stirringThe reaction mixture was stirred at 100° C. for 18 hours
  2. temperatureto cool
  3. filtrationThe solution was filtered through celite
  4. additionethyl acetate (100 mL) was added
  5. washthe organic phase was washed three times with brine (100 mL)
  6. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel (30% v/v ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-8248df4c8c054ba1aa0b657915c8d994
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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