HCID 10663122, compound → 2-(5-Bromo-2-pyridinyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one

HRID 582043Notes

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.C[Sn](C)(C)[C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][N:21]=1>CN1C(=O)CCC1.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]>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([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:21][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-3-(4-(methylsulfonyl)-phenyl)-2-cyclopenten-1-one (700 mg, 2.2 mmol), Pd2 (dba)3 (170 mg, 0.18 mmol), and the total sample of 2-trimethylstannanyl-5-bromopyridine from Step 1 was dissolved in NMP (10 mL) and degassed. The resulting solution was heated to 100° C. for 3.5 h then cooled. The mixture was diluted with EtOAc, washed 2 times with 10% NH4OH and brine, dried over MgSO4, and concentrated. The residue was purified by flash chromatography (70% EtOAc/hexanes) followed by an EtOAc/Et2O swish to provide 110 mg of the title compound.

Workup

customdegassed
temperaturethen cooled
additionThe mixture was diluted with EtOAc
washwashed 2 times with 10% NH4OH and brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by flash chromatography (70% EtOAc/hexanes)

Sources & evidence

ORD record: ord-ae7f81f0023f4e638dbc4d0a6b259ceb
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922742

Reaction notes

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