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Sodium Bicarbonate → 4-(1-(4-Chloro-2-methylphenyl)-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-oxopropyl)benzenesulfonamide

HRID 1617915
Notes
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Reaction equation

HRID 1617915 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[C:4]([CH3:20])[CH:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)O1.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]([CH:8]([C:29]2[CH:34]=[CH:33][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[C:4]([CH3:20])[CH:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 164141904-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamideHCID 666689865-[(E)-3-(4-Chloro-2-methyl-phenyl)-acryloyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 670157274-(1-(4-Chloro-2-methylphenyl)-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-oxopropyl)benzenesulfonamide

Reagents, catalysts & solvents 3

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

Procedure

In analogy to example 203, step 1, 5-[(E)-3-(4-chloro-2-methyl-phenyl)-acryloyl]-1-methyl-1H-pyridin-2-one (example 323, step 3) was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 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=445.3 [M+H]+.

Sources & evidence

ORD record
ord-b669ac1b1bfa43f98c76655e1343f7b2
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765730B2

Reaction notes

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