Bromocyclopentane → 5-Bromo-2-(cyclopentyloxy)pyridine

HRID 646143Notes

Reaction equation

HRID 646143 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH:9]1(Br)[CH2:13][CH2:12][CH2:11][CH2:10]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8728BromocyclopentaneHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 219143535-Bromo-2-(cyclopentyloxy)pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-1H-pyridin-2-one (4.0 g, 23 mmol), Ag2CO3 (3.77 g, 1.37 mmol), cyclopentyl bromide (7.4 mL, 29 mmol) and toluene (30 ml) was stirred at 60° C. for 2 days. The reaction was filtered through Celite® and the filter cake was washed with EtOAc. Concentration and vacuum distillation gave the sub-title compound (5.09 g, 92%).

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. washthe filter cake was washed with EtOAc
  3. concentrationConcentration and vacuum distillation

Sources & evidence

ORD record
ord-85f247926378474c8a0c87b198e15122
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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