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Triphenylarsine → 2-(5-Chloro-pyridin-3-yl)-3-(4-methanesulfonyl-phenyl)-cyclopent-2-enone

HRID 582038
Notes
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Reaction equation

HRID 582038 reaction equation
Br[C:2]1[C:3](=[O:17])[CH2:4][CH2:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.C1C=CC([As](C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[Sn](C)(C)[C:39]1[CH:40]=[N:41][CH:42]=[C:43]([Cl:45])[CH:44]=1>CN1C(=O)CCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:45][C:43]1[CH:44]=[C:39]([C:2]2[C:3](=[O:17])[CH2:4][CH2:5][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH:40]=[N:41][CH:42]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11773TriphenylarsineHCID 10663122HCID 10663122, compoundHCID 675529863-Trimethylstannanyl-5-chloropyridine

Product 1

HCID 106653622-(5-Chloro-pyridin-3-yl)-3-(4-methanesulfonyl-phenyl)-cyclopent-2-enoneYield 30.9%

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a degassed r.t. solution of 2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one (0.630 g, 2.0 mmol), Pd2 (dba)3 (0.037 g, 0.04 mmol), and AsPh3 (0.098 g, 0.32 mmol) in 5 mL NMP was added a degassed NMP solution (5 mL) of 3-trimethylstannanyl-5-chloropyridine (~2.0 mmol). The resulting mixture was heated to 60° C. for 16 h. The mixture was then cooled to r.t., diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated to dryness. The residue was purified by flash chromatography (80% EtOAc/hexanes) followed by a CH2Cl2 /Et2O swish to provide 0.215 g of the title compound.

Workup

  1. temperatureThe mixture was then cooled to r.t.
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash chromatography (80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fbb593b24505420b9b2442cafcd03edc
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05922742

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes