Triphenylarsine → HCID 15407933, compound

HRID 582042Notes

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][C:42]([Cl:45])=[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]>[Cl:45][C:42]1[CH:43]=[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)=[N:40][CH:41]=1

Participants

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 (0.036 g, 0.04 mmol), and AsPh3 (0.098 g, 0.32 mmol) in NMP (5 mL) was added a degassed NMP solution (8 mL) of 2-trimethylstannanyl-5-chloropyridine (~4.0 mmol). The resulting mixture was heated to 60° C. for 16 h, then to 100° C. for a further 2 h. The mixture was then cooled to r.t., diluted with EtOAc, washed 2 times with 10% NH4OH and brine, dried over MgSO4, and concentrated to dryness. The residue was purified by flash chromatography (70% EtOAc/hexanes) followed by a CH2Cl2 /Et2O swish to provide 130 mg of the title compound.

Workup

temperatureThe mixture was then cooled to r.t.
washwashed 2 times with 10% NH4OH and brine
dry with materialdried over MgSO4
concentrationconcentrated to dryness
customThe residue was purified by flash chromatography (70% EtOAc/hexanes)

Sources & evidence

ORD record: ord-d7e1f86846584d53aca07660624c3617
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922742

Reaction notes

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