Triphenylarsine → 3-(4-Methanesulfonyl-phenyl)-2-pyridin-2-yl-cyclopent-2-enone

HRID 582041Notes

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:44]=[CH:43][CH:42]=[CH:41][N:40]=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]>[N:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[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

Participants

Conditions

Temperature: 100 °C

Procedure

To a degassed r.t. solution of 2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one (1.103 g, 3.5 mmol), Pd2 (dba)3 (0.064 g, 0.07 mmol), and AsPh3 (0.171 g, 0.56 mmol) in NMP (7.5 mL) was added a degassed NMP solution (10 mL) of 2-trimethylstannanyl pyridine (~7.0 mmol). The resulting mixture was heated to 100° C. for 16 hours. The mixture was then cooled to r.t., diluted with EtOAc, washed 3 times with 10% NH4OH and brine, dried over MgSO4, and concentrated to dryness. The residue was purified by flash chromatography (5% MeOM/EtOAc) to provide 0.215 g of the title compound.

Workup

temperatureThe mixture was then cooled to r.t.
washwashed 3 times with 10% NH4OH and brine
dry with materialdried over MgSO4
concentrationconcentrated to dryness
customThe residue was purified by flash chromatography (5% MeOM/EtOAc)

Sources & evidence

ORD record: ord-31c75ef9a3134bf4a1602a67f030f591
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922742

Reaction notes

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