Sodium Bicarbonate → 5-[3-(4-Chloro-2-methyl-phenyl)-3-(3-fluoro-4-isopropoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

HRID 1617887Notes

Reaction equation

HRID 1617887 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.[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH:29]([CH3:31])[CH3:30].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:24]2[CH:25]=[CH:26][C:27]([O:28][CH:29]([CH3:30])[CH3:31])=[C:22]([F:21])[CH:23]=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 162171983-Fluoro-4-isopropoxyphenylboronic acidHCID 666689865-[(E)-3-(4-Chloro-2-methyl-phenyl)-acryloyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 666684925-[3-(4-Chloro-2-methyl-phenyl)-3-(3-fluoro-4-isopropoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-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 was reacted with 3-fluoro-4-isopropoxyphenylboronic 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=442.2 [M+H]+.

Sources & evidence

ORD record
ord-33cf3737ed584a3c82565cfaabb7bfaa
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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