Cesium carbonate → HCID 59556952, compound

HRID 1967355Notes

Reaction equation

HRID 1967355 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.[F:12][C:13]1([F:21])[C@H:17]([OH:18])[C@H:16]([CH3:19])[NH:15][C:14]1=[O:20].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]>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([N:15]2[C@@H:16]([CH3:19])[C@@H:17]([OH:18])[C:13]([F:21])([F:12])[C:14]2=[O:20])[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 223467024-Bromo-2-methoxybenzonitrileHCID 59556931HCID 59556931, compound

Product 1

HCID 59556952HCID 59556952, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-methoxybenzonitrile (2.34 g), (4R,5S)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one (2.00 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (976 mg), tris(dibenzylideneacetone)dipalladium(0) (504 mg) and cesium carbonate (5.30 g), and in the same manner as in Reference Example 18, the title compound was obtained as a colorless solid (yield: 201 mg, 7%).

Sources & evidence

ORD record
ord-7f9287a928b245f4aac6a706e3795e84
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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