1,3-Dichloro-5,6-dihydro-4H-cyclopenta(c)thiophen-4-one → HCID 17764632, compound

HRID 2121717Notes

Reaction equation

HRID 2121717 reaction equation
Cl[C:2]1[S:3][C:4](Cl)=[C:5]2[C:9](=[O:10])[CH2:8][CH2:7][C:6]=12.[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:12]1[CH:17]=[CH:16][C:15]([C:2]2[S:3][C:4]([C:15]3[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=3)=[C:5]3[C:9](=[O:10])[CH2:8][CH2:7][C:6]=23)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 3156161,3-Dichloro-5,6-dihydro-4H-cyclopenta(c)thiophen-4-oneHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 17764632HCID 17764632, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 1,3-dichloro-5,6-dihydro-4H-cyclopenta(c)thiophen-4-one (923 mg, 4.45 mmol) in dimethoxyethane (23 mL) was added 4-pyridineboronic acid (1.3 g, 10.6 mmol), saturated aqueous NaHCO3 solution (7.5 mL), and bis(triphenylphosphine)palladium chloride (350 mg, 0.49 mmol) under nitrogen. The mixture was heated at reflux temperature for 36 hours. The reaction mixture wvas filtered through celite and the filtrate was extracted with ethyl acetate (100 mL×5). The combined organic layer was washed with brine (100 mL), dried over MgSO4, and concentrated in vacuo. Chromatographic purification eluting with dichloromethane/methanol (25:1) and the subsequent recrystallization from ethyl acetate/hexane gave the title compound (645 mg, 50% yield) as yellow solids.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 36 hours
  3. filtrationThe reaction mixture wvas filtered through celite
  4. extractionthe filtrate was extracted with ethyl acetate (100 mL×5)
  5. washThe combined organic layer was washed with brine (100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification
  9. washeluting with dichloromethane/methanol (25:1)
  10. customthe subsequent recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-27fe893c33894e419a1d851bb1ef5441
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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