Bromocyclopentane → Methyl 5-(cyclopentyloxy)-6-methoxy-3-pyridinecarboxylate

HRID 993285Notes

Reaction equation

HRID 993285 reaction equation
[OH:1][C:2]1[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH:20]1(Br)[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C)C=O.O>[CH:20]1([O:1][C:2]2[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 22145686HCID 22145686, compound

Product 1

HCID 22145812Methyl 5-(cyclopentyloxy)-6-methoxy-3-pyridinecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 5-hydroxy-6-methoxynicotinoate (250 mg), anhydrous potassium carbonate (600 mg) and cyclopentyl bromide (0.26 mL) in dry dimethylformamide (5 mL) is stirred and heated at 60±5° C. for 24 hours. The mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The extracts are washed with water and dried (MgSO4). Concentration gave methyl 5-cyclopentyloxy-6-methoxynicotinoate (290 mg) as an oil.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-6499f451c12e4ba2889f3520bdfc7fd0
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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