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

HRID 1173555Notes

Reaction equation

HRID 1173555 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[CH2:11]([CH:13]1[NH:17][C:16](=[O:18])[C:15]([CH3:20])([CH3:19])[C:14]1=[O:21])[CH3:12].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]>[Cl:10][C:4]1[CH:3]=[C:2]([N:17]2[CH:13]([CH2:11][CH3:12])[C:14](=[O:21])[C:15]([CH3:20])([CH3:19])[C:16]2=[O:18])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70104204-Bromo-2-chlorobenzonitrileHCID 595570275-Ethyl-3,3-dimethylpyrrolidine-2,4-dione

Product 1

HCID 595570162-Chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-chlorobenzonitrile (219 mg), 5-ethyl-3,3-dimethylpyrrolidine-2,4-dione (120 mg), cesium carbonate (378 mg), tris(dibenzylideneacetone)dipalladium(0) (71 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (89 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a colorless solid (yield: 147 mg, 65%).

Sources & evidence

ORD record
ord-946f77b0c0ee40df90ab8344e2ba8f66
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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