Cesium carbonate → [5-(Furan-2-yl)pyridin-3-yl]methanol

HRID 385595Notes

Reaction equation

HRID 385595 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1B(O)O.[Cl-].[Li+].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 433294Lithium ChlorideHCID 2734357Furan-2-boronic acidHCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 24729849[5-(Furan-2-yl)pyridin-3-yl]methanolYield 41.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.10 g of (5-bromopyridin-3-yl)methanol in 5 mL of dioxane, 72 mg of 2-furanboronic acid, 67 mg of lithium chloride, 0.51 g of cesium carbonate, 5.4 mg of palladium acetate and 20 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl were added at room temperature, and the mixture was heated under reflux for 1 hour 30 minutes under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was then distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=95:5 to 90:10 to obtain 39 mg of (5-(2-furyl)pyridin-3-yl)methanol as a yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour 30 minutes under a nitrogen atmosphere
  3. distillationthe solvent was then distilled off under reduced pressure
  4. customThe resultant residue was purified by flash silica gel column chromatography
  5. washelution with chloroform

Sources & evidence

ORD record
ord-399de85177a64d5d9c02a3609fd8c7eb
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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