Sodium Bicarbonate → 5-(3-(4-chloro-2-methylphenyl)-3-(4-(hydroxymethyl)phenyl)propanoyl)-1-methylpyridin-2(1H)-one

HRID 1617913Notes

Reaction equation

HRID 1617913 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.[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.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:26]2[CH:27]=[CH:28][C:23]([CH2:22][OH:21])=[CH:24][CH:25]=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

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 666689865-[(E)-3-(4-Chloro-2-methyl-phenyl)-acryloyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 666690635-(3-(4-chloro-2-methylphenyl)-3-(4-(hydroxymethyl)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, 5-[(E)-3-(4-chloro-2-methyl-phenyl)-acryloyl]-1-methyl-1H-pyridin-2-one (example 323, step 3) was reacted with 4-(hydroxymethyl)phenyl-boronic 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 yellow foam, MS (ESI+): m/z=396.1 [M+H]+.

Sources & evidence

ORD record
ord-7cbb9d1cf1f1416ab48a94fb09754a09
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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