Cesium carbonate → 2-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxopyrrolidin-1-yl]benzonitrile

HRID 1173686Notes

Reaction equation

HRID 1173686 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[OH:11][C@:12]1([CH3:19])[C@H:16]([CH3:17])[NH:15][C:14](=[O:18])[CH2:13]1.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.C(=O)([O-])[O-].[Cs+].[Cs+]>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:15]2[C:14](=[O:18])[CH2:13][C@@:12]([OH:11])([CH3:19])[C@@H:16]2[CH3:17])[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 55299894(4S,5S)-4-hydroxy-4,5-dimethylpyrrolidin-2-one

Product 1

HCID 595570202-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxopyrrolidin-1-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-chlorobenzonitrile (615 mg), (4S,5S)-4-hydroxy-4,5-dimethylpyrrolidin-2-one (423 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (241 mg), tris(dibenzylideneacetone)dipalladium(0) (125 mg) and cesium carbonate (1.31 g), and in the same manner as in Reference Example 18, the title compound was obtained as a colorless solid (yield: 431 mg, 60%).

Sources & evidence

ORD record
ord-71e0541746aa452daaf569d48d29c132
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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