Isobutanol → HCID 61375113, compound

HRID 1620324Notes

Reaction equation

HRID 1620324 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].[H-].[Na+].[Br:8][C:9]1[CH:10]=[CH:11][C:12](F)=[N:13][CH:14]=1>CN(C=O)C.O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:4][CH2:3][CH:2]([CH3:5])[CH3:1])=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 61375113HCID 61375113, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 2-methyl-propan-1-ol (10 g, 0.41 mol) was added NaH (60%, 8.2 g, 0.204 mol) portionwise under a nitrogen atmosphere at room temperature over 10 minutes. The mixture was refluxed for 30 minutes. A solution of 5-bromo-2-fluoro-pyridine (24 g, 0.136 mol) in DMF (400 mL) was added dropwise and the mixture refluxed for 18 hours. The reaction mixture was then diluted with water (1 L) and extracted with EtOAc (3×500 mL). The combined organics were washed with brine (3×300 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue obtained was purified by flash column chromatography eluting with petroleum ether to yield the title compound as a colourless oil (27 g).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperaturethe mixture refluxed for 18 hours
  3. extractionextracted with EtOAc (3×500 mL)
  4. washThe combined organics were washed with brine (3×300 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue obtained
  9. customwas purified by flash column chromatography
  10. washeluting with petroleum ether

Sources & evidence

ORD record
ord-6ef68ccd4d204eae9af74f18bff5f832
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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