Cesium carbonate → Rac-2-chloro-4-[(4r,5r)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

HRID 1173563Notes

Reaction equation

HRID 1173563 reaction equation
[Si:1]([O:8][CH:9]1[CH:13]([CH3:14])[NH:12][C:11](=[O:15])[C:10]1([CH3:17])[CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[CH:20]=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:27][C:21]1[CH:20]=[C:19]([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])[C:10]([CH3:16])([CH3:17])[C:11]2=[O:15])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

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 67105615(4RS,5RS)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one

Product 1

HCID 67105796Rac-2-chloro-4-[(4r,5r)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using (4RS,5RS)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one (380 mg), 4-bromo-2-chlorobenzonitrile (320 mg), cesium carbonate (722 mg), tris(dibenzylideneacetone)dipalladium(0) (68 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (85 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a colorless solid (yield: 400 mg, 69%).

Sources & evidence

ORD record
ord-e2f6e5116e404334bcedc2deeac5547b
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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