Cesium carbonate → HCID 59556916, compound

HRID 1967400Notes

Reaction equation

HRID 1967400 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[CH:11]1([C@@:14]2([OH:22])[C@H:18]([CH2:19][CH3:20])[NH:17][C:16](=[O:21])[CH2:15]2)[CH2:13][CH2:12]1.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:16](=[O:21])[CH2:15][C@:14]([CH:11]3[CH2:13][CH2:12]3)([OH:22])[C@@H:18]2[CH2:19][CH3:20])[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 70104204-Bromo-2-chlorobenzonitrileHCID 57577515HCID 57577515, compound

Product 1

HCID 59556916HCID 59556916, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-chlorobenzonitrile (389 mg), (4R,5S)-4-cyclopropyl-5-ethyl-4-hydroxypyrrolidin-2-one (350 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (153 mg), tris(dibenzylideneacetone)dipalladium(0) (79 mg) and cesium carbonate (786 mg), and in the same manner as in Example 62, the title compound was obtained as pale-yellow crystals (yield: 104 mg, 20%).

Sources & evidence

ORD record
ord-de5c7e0732484c54b7de7e183532c4a1
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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