Cesium carbonate → HCID 59556938, compound

HRID 1173731Notes

Reaction equation

HRID 1173731 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[CH2:11]([C@@H:13]1[NH:17][C:16](=[O:18])[C:15]([F:20])([F:19])[C@@H:14]1[OH:21])[CH3:12].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:10][C:4]1[CH:3]=[C:2]([N:17]2[C@@H:13]([CH2:11][CH3:12])[C@@H:14]([OH:21])[C:15]([F:20])([F:19])[C:16]2=[O:18])[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 70104204-Bromo-2-chlorobenzonitrileHCID 57577519(4R,5S)-5-ethyl-3,3-difluoro-4-hydroxypyrrolidin-2-one

Product 1

HCID 59556938HCID 59556938, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-chlorobenzonitrile (2.28 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 pale-yellow crystals (yield: 153 mg, 10%).

Sources & evidence

ORD record
ord-9865d45f887b44a3a9bf401903d5ed6c
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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