Ethyl 3-(3,5-dibromopyridin-4-yl)propanoate → 4-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-one

HRID 714060Notes

Reaction equation

HRID 714060 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:15])[C:7]=1[CH2:8][CH2:9][C:10]([O:12]CC)=O.[Li]CCCC>C1COCC1>[Br:15][C:6]1[C:7]2[CH2:8][CH2:9][C:10](=[O:12])[C:2]=2[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 86685955Ethyl 3-(3,5-dibromopyridin-4-yl)propanoateHCID 178418339Butyllithium

Product 1

HCID 717438924-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-oneYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 3-(3,5-dibromopyridin-4-yl)propanoate (30 g, 89 mmol) in THF (50 mL) was added slowly n-BuLi (71.2 mL, 178 mmol, 2.5 M in hexane) at −78° C. The resulting mixture was stirred for another 30 min at −78° C. before it was quenched with water, and extracted with EtOAc (500 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by column chromatography (n-pentane:EtOAc=5:1) to give title compound (7 g, 37%) as a white solid. MS: 211.8 (M+H+, 1 Br).

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc (500 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas purified by column chromatography (n-pentane:EtOAc=5:1)

Sources & evidence

ORD record
ord-907e1e664701485fa769eea6e1eede3f
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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