Potassium Carbonate → 4-(3-Bromo-furan-2-yl)-pyridine

HRID 271509Notes

Reaction equation

HRID 271509 reaction equation
Br[C:2]1[O:3][CH:4]=[CH:5][C:6]=1[Br:7].[N:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:7][C:6]1[CH:5]=[CH:4][O:3][C:2]=1[C:11]1[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734379(Pyridin-4-yl)boronic acidHCID 70215012,3-Dibromofuran

Product 1

HCID 157218314-(3-Bromo-furan-2-yl)-pyridineYield 54%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A degassed mixture of 2,3-dibromofuran (11.3 g, 50 mmol), 4-pyridyl boronic acid (M. Lamothe et al, J. Med. Chem., 1997, 40, 3542) (6.15 g, 50 mmol) and potassium carbonate (55 g, 0.4 mol) in ethylene glycol dimethyl ether (300 ml) and water (150 ml) was treated with triphenylphosphine (1.31 g, 5 mmol) and palladium acetate (625 mg, 2.5 mmol) then heated under reflux for 18 hours. After cooling to room temperature, the mixture was filtered through filter aid and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and brine, dried, concentrated in vacuo and the residue purified by silica gel chromatography to give the title compound (6.0 g, 54%); MS(ES+) m/e 224/226 [M+H]+.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 18 hours
  3. filtrationthe mixture was filtered
  4. filtrationthrough filter aid
  5. additionthe filtrate diluted with water and ethyl acetate
  6. customThe organic phase was separated
  7. washwashed with water and brine
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e621bab50a446d88380f65519c7033d
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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