Sodium Bicarbonate → 5-(3-(2,5-Dichlorophenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-methylpyridin-2(1H)-one

HRID 1617943Notes

Reaction equation

HRID 1617943 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12].[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:24])=[O:23].C(=O)([O-])O.[Na+]>O1CCOCC1.O.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:28]1[CH:29]=[CH:30][C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:26][CH:27]=1)[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 66668982(E)-5-(3-(2,5-Dichlorophenyl)acryloyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 666689515-(3-(2,5-Dichlorophenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In analogy to example 203, step 1, (E)-5-(3-(2,5-dichlorophenyl)acryloyl)-1-methylpyridin-2(1H)-one was reacted with 4-(methylsulfonyl)phenylboronic acid in the presence of chloro(1,5-cyclooctadiene)rhodium(I) dimer and sodium hydrogencarbonate in 1,4-dioxane and water at 60° C. to give the title compound as a colourless solid, MS (ESI+): m/z=464.1 [M+H]+.

Sources & evidence

ORD record
ord-dc3b7323bbb9411e8ae794a4bb4da63d
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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