Diethyl Ether → 4-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-one

HRID 714045Notes

Reaction equation

HRID 714045 reaction equation
[Br:1][C:2]1[C:3]2[CH2:10][C:9](C(OC)=O)=[C:8]([O-:15])[C:4]=2[CH:5]=[N:6][CH:7]=1.[Na+].CCOCC.[OH-].[K+]>Cl>[Br:1][C:2]1[C:3]2[CH2:10][CH2:9][C:8](=[O:15])[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 86699309sodium 4-bromo-6-(methoxycarbonyl)-5H-cyclopenta[c]pyridin-7-olate

Product 1

HCID 717438924-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-oneYield 16.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The crude sodium 4-bromo-6-(methoxycarbonyl)-5H-cyclopenta[c]pyridin-7-olate (20.0 mmol) was dissolved in aq. 6 M HCl, (54 mL) and heated at reflux for 1.5 h. The acidic solution was cooled in ice, poured into Et2O, basified with aq. 6 M KOH (to give a pH of −9) and extracted with Et2O (2×). The Et2O phases were collected, dried over Na2SO4, concentrated and purified by flash chromatography (20 g SiO2, i-PrOH (1%)/CH2Cl2) to afford after trituration with a small amount of Et2O the title compound (0.69 g, 16% over 2 steps) as pink solid. MS: 212.0 (M+H−, 1 Br).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe acidic solution was cooled in ice
  4. customto give a pH of −9) and
  5. extractionextracted with Et2O (2×)
  6. customThe Et2O phases were collected
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by flash chromatography (20 g SiO2, i-PrOH (1%)/CH2Cl2)

Sources & evidence

ORD record
ord-c4a00bcadc134c4f93e408383d181984
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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