HCID 86684813, compound → HCID 86684812, compound

HRID 1527981Notes

Reaction equation

HRID 1527981 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9]2([CH2:14][C@H:15]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])OCC[O:10]2)=[N:3]1>CC(C)=O.CC#N.CC#N.Cl[Pd]Cl>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9](=[O:10])[CH2:14][C@H:15]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[N:3]1

Participants

4

Reactant 1

HCID 86684813HCID 86684813, compound

Product 1

HCID 86684812HCID 86684812, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalyst2×HCID 180AcetoneSolvent

Procedure

To a solution of (R)-2-methyl-6-(2-(2-(4-(methylsulfonyl)phenyl)-2-o-tolylethyl)-1,3-dioxolan-2-yl)pyridazin-3(2H)-one (10 mg, 22 μmol) in acetone (1 ml) was added bis(acetonitrile)dichloropalladium(II) (1.4 mg, 5 μmol, Eq: 0.25), then after 24 h at room temperature another portion of bis(acetonitrile)dichloropalladium(II) (6 mg, 22 μmol) was added, then after 24 h the reaction mixture was evaporated. Chromatography (SiO2; gradient heptane/ethyl acetate 2:1 to ethyl acetate) afforded the title compound (5 mg, 55%). White solid, MS: 411.2 [M+H]+.

Workup

  1. customafter 24 h the reaction mixture was evaporated

Sources & evidence

ORD record
ord-c5221bd44f7840529aff8a88185374f6
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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