Water → HCID 11311040, compound

HRID 496808Notes

Reaction equation

HRID 496808 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.Br[CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.O>CN(C)C=O>[Br:3][C:4]1[C:9]([O:10][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydride

Product 1

HCID 11311040HCID 11311040, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (160 mg) was dissolved in dimethylformamide (5 ml) and 2-bromo-3-pyridinol (500 mg) dissolved in dimethylformamide is slowly added dropwise. Then, bromocyclopentane (0.63 ml) was added to the solution and reacted for 5 hours at room temperature. Water was added to the suspension to dilute and extracted with ethyl acetate to separate an organic layer. The separated organic layer was dried with anhydrous magnesium sulfate and distilled under reduced pressure. As a result, 2-bromo-3-cyclopentyloxy pyridine (480 mg, yield: 60%) was obtained as an oil phase.

Workup

  1. additionis slowly added dropwise
  2. customreacted for 5 hours at room temperature
  3. additionto dilute
  4. extractionextracted with ethyl acetate
  5. customto separate an organic layer
  6. dry with materialThe separated organic layer was dried with anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-0e8f5b95a1354e788d4fd91a9ea40e85
Source dataset
uspto-grants-2005_09
Patent number
US06946558B2

Reaction notes

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