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

HRID 1173724Notes

Reaction equation

HRID 1173724 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](I)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:12]([C@@H:14]1[NH:18][C:17](=[O:19])[CH2:16][C@@:15]1([OH:21])[CH3:20])[CH3:13].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:1][C:2]1[C:9]([CH3:10])=[C:8]([N:18]2[C:17](=[O:19])[CH2:16][C@@:15]([OH:21])([CH3:20])[C@@H:14]2[CH2:12][CH3:13])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 167319952-Chloro-4-iodo-3-methylbenzonitrileHCID 55299895(4S,5S)-5-ethyl-4-hydroxy-4-methylpyrrolidin-2-one

Product 1

HCID 595568952-chloro-4-[(2S,3S)-2-ethyl-3-hydroxy-3-methyl-5-oxopyrrolidin-1-yl]-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 2-chloro-4-iodo-3-methylbenzonitrile (565 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: 132 mg, 22%).

Sources & evidence

ORD record
ord-d45859d89b7f4bd89c94bb0c53c2e717
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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