Cesium carbonate → HCID 59556921, compound

HRID 1967282Notes

Reaction equation

HRID 1967282 reaction equation
[Si:1]([O:8][CH:9]1[C:13]2([CH2:15][CH2:14]2)[C:12](=[O:16])[NH:11][C@H:10]1[CH3:17])([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:13]2([CH2:14][CH2:15]2)[C:12](=[O:16])[N:11]([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@H:10]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:1]([O:8][C@H:9]1[C:13]2([CH2:14][CH2:15]2)[C:12](=[O:16])[N:11]([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@H:10]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

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 58238347HCID 58238347, compound

Product 2

HCID 59556921HCID 59556921, compoundYield 56%HCID 67105223HCID 67105223, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using (6S)-7-(tert-butyldimethylsilyloxy)-6-methyl-5-azaspiro[2.4]heptan-4-one (720.5 mg), 4-iodo-2-trifluoromethylbenzonitrile (921.3 mg), cesium carbonate (1.38 g), tris(dibenzylideneacetone)dipalladium(0) (129 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (326 mg), and in the same manner as in Reference Example 3, the title compound (yield: 670 mg, yield 56%) and 4-[(6S,7S)-7-(tert-butyldimethylsilyloxy)-6-methyl-4-oxo-5-azaspiro[2.4]hept-5-yl]-2-(trifluoromethyl)benzonitrile (yield: 309 mg, 26%) were obtained each as a colorless solid.

Sources & evidence

ORD record
ord-a130ed45b79147b896592ffa315fac70
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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