Potassium Carbonate → 5-(3-(4-Chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-(2-(2-methoxyethoxy)ethyl)pyridin-2(1H)-one

HRID 1617918Notes

Reaction equation

HRID 1617918 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:18])[NH:16][CH:17]=2)=[O:11])=[C:4]([CH3:29])[CH:3]=1.Br[CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:18])[N:16]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])[CH:17]=2)=[O:11])=[C:4]([CH3:29])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 670157545-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)pyridin-2(1H)-one

Product 1

HCID 666687605-(3-(4-Chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-(2-(2-methoxyethoxy)ethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

In analogy to example 161, step 1, 5-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)pyridin-2(1H)-one was reacted with 1-bromo-2-(2-methoxyethoxy)ethane in the presence of potassium carbonate and a catalytic amount of tetrabutylammonium iodide to give the title compound as a light brown oil, MS (ESI+): m/z=532.2 [M+H]+.

Sources & evidence

ORD record
ord-18a5ba5985e24649b859c9e1bfff9bb7
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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