Sodium Bicarbonate → HCID 66669030, compound

HRID 1617948Notes

Reaction equation

HRID 1617948 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([C:13]2[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:24])=[O:23].C(=O)([O-])O.[Na+]>O1CCOCC1.O.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[F:8][C:6]1[CH:5]=[C:4]([CH:9]([C:28]2[CH:29]=[CH:30][C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:26][CH:27]=2)[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 66668223HCID 66668223, compound

Product 1

HCID 66669030HCID 66669030, compound

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, (E)-5-(3-(3,5-difluorophenyl)acryloyl)-1-methylpyridin-2(1H)-one was reacted with 4-(methylsulfonyl)phenylboronic 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 solid, MS (ESI+): m/z=432.3 [M+H]+.

Sources & evidence

ORD record
ord-41134ae9108641f29b1a43c949cad3e0
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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