Sodium hydride → 5-Bromo-3-chloro-2-(cyclopropylmethoxy)pyridine

HRID 2277162Notes

Reaction equation

HRID 2277162 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Br:8][C:9]1[CH:10]=[C:11]([Cl:16])[C:12](Cl)=[N:13][CH:14]=1>CN(C=O)C.C(OCC)(=O)C.O>[Br:8][C:9]1[CH:10]=[C:11]([Cl:16])[C:12]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:13][CH:14]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 127477605-Bromo-2,3-dichloropyridine

Product 1

HCID 867312155-Bromo-3-chloro-2-(cyclopropylmethoxy)pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclopropylmethanol (4.64 mL) in DMF (100 mL) was added sodium hydride (60% oil, 2.29 g), and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added 5-bromo-2,3-dichloropyridine (10.0 g), and the mixture was stirred with heating at 70° C. for 30 min. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate and water, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (8.11 g).

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating at 70° C. for 30 min
  3. temperatureto cool to room temperature
  4. customthe organic layer was separated
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6fdc94ec93ef40ae91163b8984e13586
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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