Cesium carbonate → HCID 59557006, compound

HRID 1967273Notes

Reaction equation

HRID 1967273 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H: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].I[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[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]>[Si:1]([O:8][C@@H:9]1[C@H:13]([CH3:14])[N:12]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:28])([F:30])[F:29])[CH:20]=2)[C:11](=[O:15])[C:10]1([CH3:16])[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 162183374-Iodo-2-(trifluoromethyl)benzonitrileHCID 59556936HCID 59556936, compound

Product 1

HCID 59557006HCID 59557006, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using (4S,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one (161.8 mg), 4-iodo-2-(trifluoromethyl)benzonitrile (205 mg), cesium carbonate (307 mg), tris(dibenzylideneacetone)dipalladium(0) (30 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (73 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a colorless solid (yield: 232.2 mg, yield: 87%).

Sources & evidence

ORD record
ord-8364cbeedb054392a8194727efe20280
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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