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

HRID 1173554Notes

Reaction equation

HRID 1173554 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](I)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].NC1C=CC(C#N)=C(Cl)C=1C.[CH3:23][C:24]1([CH3:32])[C:28](=[O:29])[CH:27]([CH3:30])[NH:26][C:25]1=[O:31].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:1][C:2]1[C:9]([CH3:10])=[C:8]([N:26]2[CH:27]([CH3:30])[C:28](=[O:29])[C:24]([CH3:32])([CH3:23])[C:25]2=[O:31])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 167319952-Chloro-4-iodo-3-methylbenzonitrileHCID 218754134-Amino-2-chloro-3-methylbenzonitrileHCID 552998933,3,5-Trimethylpyrrolidine-2,4-dione

Product 1

HCID 595569842-Chloro-3-methyl-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 2-chloro-4-iodo-3-methylbenzonitrile (894 mg) synthesized from 4-amino-2-chloro-3-methylbenzonitrile in the same method as in Reference Example 8, 3,3,5-trimethylpyrrolidine-2,4-dione (350 mg), cesium carbonate (1.21 g), tris(dibenzylideneacetone)dipalladium(0) (227 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (287 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a colorless solid (yield: 46 mg, 6%).

Sources & evidence

ORD record
ord-999526287c5b4554b50d6fe1224b60eb
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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