Cesium carbonate → 2-chloro-4-[(4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-oxopyrrolidin-1-yl]benzonitrile

HRID 1967245Notes

Reaction equation

HRID 1967245 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([CH3:14])[NH:12][C:11](=[O:15])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([Cl:25])[CH:18]=1.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:25][C:19]1[CH:18]=[C:17]([N:12]2[C@@H:13]([CH3:14])[C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][C:11]2=[O:15])[CH:24]=[CH:23][C:20]=1[C:21]#[N:22]

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 59556992HCID 59556992, compound

Product 1

HCID 595568912-chloro-4-[(4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-oxopyrrolidin-1-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one (1.06 g), 4-bromo-2-chlorobenzonitrile (1.0 g), cesium carbonate (2.25 g), tris(dibenzylideneacetone)dipalladium(0) (210 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (399 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a colorless solid (yield: 1.2 g, 71%).

Sources & evidence

ORD record
ord-2dc64e716b8e4309ad68f0e45595b108
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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