3-bromo-2-chloro-5-(4-ethylpiperazin-1-ylsulfonyl)pyridine → HCID 22052242, compound

HRID 1355561Notes

Reaction equation

HRID 1355561 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.[O-:20][CH2:21][CH3:22].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([O:20][CH2:21][CH3:22])=[N:4][CH:5]=[C:6]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 10342243-bromo-2-chloro-5-(4-ethylpiperazin-1-ylsulfonyl)pyridineHCID 2723922Sodium ethoxide

Product 1

HCID 22052242HCID 22052242, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-bromo-2-chloro-5-(4-ethylpiperazin-1-ylsulfonyl)pyridine (Preparation 9; 6.60 g, 17.9 mmol) and sodium ethoxide (6.09 g, 89.55 mmol) in ethanol (100 mL) was heated under reflux for 18 hours, then cooled. The reaction mixture was concentrated under reduced pressure, the residue partitioned between water (100 mL) and ethyl acetate (100 mL), and the layers separated. The aqueous phase was extracted with ethyl acetate (2×100 mL), the combined organic solutions dried (MgSO4) and evaporated under reduced pressure to afford the title compound as a brown solid (6.41 g, 95%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperaturecooled
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue partitioned between water (100 mL) and ethyl acetate (100 mL)
  6. customthe layers separated
  7. extractionThe aqueous phase was extracted with ethyl acetate (2×100 mL)
  8. dry with materialthe combined organic solutions dried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-573457d8934d43cfaac7905f5b6006bf
Source dataset
uspto-grants-2003_07
Patent number
US06586439B2

Reaction notes

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