2-Bromopyridine → HCID 49761854, compound

HRID 1712930Notes

Reaction equation

HRID 1712930 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[Zn][C:10]1[O:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:14]=1>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:10]1[O:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 79732-BromopyridineHCID 178469114HCID 178469114, compound

Product 1

HCID 49761854HCID 49761854, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-bromopyridine (1.4 mL, 15 mmol) and bromo[5-(ethoxycarbonyl)-2-furyl]zinc (0.5 M in THF, 30 mL) was degassed. To this mixture was added tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol). The reaction mixture was allowed to stir at 70° C. overnight and then to cool to rt. The mixture was diluted with EtOAc and washed with aq. Sat. NaHCO3. A precipitate formed and was filtered. The filtrate was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give ethyl 5-pyridin-2-yl-2-furoate (2.02 g, 62%). LCMS: (FA) ES+ 218.

Workup

  1. customwas degassed
  2. temperatureto cool to rt
  3. washwashed with aq. Sat. NaHCO3
  4. customA precipitate formed
  5. filtrationwas filtered
  6. washThe filtrate was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-824381a4d99149928e34404952f5d9b7
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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