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

HRID 1967394Notes

Reaction equation

HRID 1967394 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[CH2:11]([C@@H:13]1[NH:17][C:16](=[O:18])[CH2:15][C@@:14]1([OH:20])[CH3:19])[CH3:12].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:17]2[C:16](=[O:18])[CH2:15][C@@:14]([OH:20])([CH3:19])[C@@H:13]2[CH2:11][CH3:12])[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 55299895(4S,5S)-5-ethyl-4-hydroxy-4-methylpyrrolidin-2-one

Product 1

HCID 595569402-chloro-4-[(2S,3S)-2-ethyl-3-hydroxy-3-methyl-5-oxopyrrolidin-1-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-chlorobenzonitrile (459 mg), (4S,5S)-5-ethyl-4-hydroxy-4-methylpyrrolidin-2-one (350 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (180 mg), tris(dibenzylideneacetone)dipalladium(0) (93 mg) and cesium carbonate (929 mg), and in the same manner as in Example 62, the title compound was obtained as colorless crystals (yield: 318 mg, 56%).

Sources & evidence

ORD record
ord-753cb1dde1bb47fbb2e202b3b955f9a3
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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