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

HRID 2277662Notes

Reaction equation

HRID 2277662 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 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(3,5-dibromopyridin-4-yl)propanoate (4 g, 11.9 mmol) in THF (60 mL) was slowly added n-BuLi (9.52 mL, 23.8 mmol, 2.5 M in hexane) while keeping the inner temperature below −70° C. After the addition, the reaction mixture was stirred below −65° C. for additional 2 hours. The reaction was quenched with water and then extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The residue was then purified by column chromatography to afford the title compound (1.2 g, 47.6%) as a solid. MS: MS: 213.7 (M+H+, 1Br).

Workup

  1. customthe inner temperature below −70° C
  2. additionAfter the addition
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc (100 mL×3)
  5. customThe combined organic layers were dried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-640ac978ee8545a8bfc2a123f2011481
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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