Cesium carbonate → 4-(5-Ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-2-(trifluoromethyl)benzonitrile

HRID 1173557Notes

Reaction equation

HRID 1173557 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH2:14]([CH:16]1[NH:20][C:19](=[O:21])[C:18]([CH3:23])([CH3:22])[C:17]1=[O:24])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:14]([CH:16]1[N:20]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=2)[C:19](=[O:21])[C:18]([CH3:23])([CH3:22])[C:17]1=[O:24])[CH3:15]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 162183374-Iodo-2-(trifluoromethyl)benzonitrileHCID 595570275-Ethyl-3,3-dimethylpyrrolidine-2,4-dione

Product 1

HCID 595570054-(5-Ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-iodo-2-(trifluoromethyl)benzonitrile (526 mg), 5-ethyl-3,3-dimethylpyrrolidine-2,4-dione (250 mg), cesium carbonate (787 mg), tris(dibenzylideneacetone)dipalladium(0) (148 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (186 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a pale-yellow oil (yield: 298 mg, 57%).

Sources & evidence

ORD record
ord-247c49795ad041e091f74bfa91b35362
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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