Cesium carbonate → 4-{4-[1-(4-Chloro-2-methyl-phenyl)-3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-propyl]-2-fluoro-phenoxy}-butyric acid methyl ester

HRID 1617895Notes

Reaction equation

HRID 1617895 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=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]([CH3:28])[CH:3]=1.Br[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[CH3:36][O:35][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:28])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[CH:21][C:22]=1[F:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 666691835-[3-(4-Chloro-2-methyl-phenyl)-3-(3-fluoro-4-hydroxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 666683464-{4-[1-(4-Chloro-2-methyl-phenyl)-3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-propyl]-2-fluoro-phenoxy}-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In analogy to example 221, step 6, 5-[3-(4-chloro-2-methyl-phenyl)-3-(3-fluoro-4-hydroxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one (example 324, step 1) was reacted with methyl 4-bromobutyrate in N,N-dimethylacetamide in the presence of cesium carbonate to give the title compound as a colourless foam, MS (ESI+): m/z=500.3 [M+H]+.

Sources & evidence

ORD record
ord-89e1fdbd02d6463cbc3dee6083f94386
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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