Cesium carbonate → HCID 59556877, compound

HRID 1967403Notes

Reaction equation

HRID 1967403 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH2:12]([C@@H:14]1[NH:18][C:17](=[O:19])[C:16]([F:21])([F:20])[C@@H:15]1[OH:22])[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]>[CH2:12]([C@@H:14]1[N:18]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=2)[C:17](=[O:19])[C:16]([F:20])([F:21])[C@@H:15]1[OH:22])[CH3:13]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 223467024-Bromo-2-methoxybenzonitrileHCID 57577519(4R,5S)-5-ethyl-3,3-difluoro-4-hydroxypyrrolidin-2-one

Product 1

HCID 59556877HCID 59556877, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-methoxybenzonitrile (2.14 g), (4R,5S)-5-ethyl-3,3-difluoro-4-hydroxypyrrolidin-2-one (2.00 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (954 mg), tris(dibenzylideneacetone)dipalladium(0) (554 mg) and cesium carbonate (4.84 g), and in the same manner as in Example 62, the title compound was obtained as a white powder (yield: 895 mg, 30%).

Sources & evidence

ORD record
ord-51e4174e2ccc48f683621b1b9923cafc
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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