Cesium carbonate → 2,6-Difluoro-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile

HRID 1967234Notes

Reaction equation

HRID 1967234 reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]1([CH3:21])[C:17](=[O:18])[CH:16]([CH3:19])[NH:15][C:14]1=[O:20].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]>[F:10][C:8]1[CH:9]=[C:2]([N:15]2[CH:16]([CH3:19])[C:17](=[O:18])[C:13]([CH3:21])([CH3:12])[C:14]2=[O:20])[CH:3]=[C:4]([F:11])[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 27569164-Bromo-2,6-difluorobenzonitrileHCID 552998933,3,5-Trimethylpyrrolidine-2,4-dione

Product 1

HCID 595569512,6-Difluoro-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2,6-difluorobenzonitrile (502 mg), 3,3,5-trimethylpyrrolidine-2,4-dione (250 mg), cesium carbonate (866 mg), tris(dibenzylideneacetone)dipalladium(0) (162 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (205 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a colorless solid (yield: 305 mg, 62%).

Sources & evidence

ORD record
ord-073ef31d1325435ca95d9956446fc88b
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

Loading…