Sodium Bicarbonate → HCID 66668499, compound

HRID 1617871Notes

Reaction equation

HRID 1617871 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]([F:20])[CH:3]=1.[CH2:21]([S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH3:22].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:29]2[CH:28]=[CH:27][C:26]([S:23]([CH2:21][CH3:22])(=[O:25])=[O:24])=[CH:31][CH:30]=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]([F:20])[CH:3]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27734204-(Ethylsulphonyl)benzeneboronic acidHCID 66668501HCID 66668501, compound

Product 1

HCID 66668499HCID 66668499, 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-(4-chloro-2-fluorophenyl)acryloyl)-1-methyl-pyridin-2(1H)-one (example 314, step 2) was reacted with 4-(ethylsulfonyl)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 foam, MS (ESI+): m/z=462.2 [M+H]+.

Sources & evidence

ORD record
ord-1ec171c7ee0245c699f4a86bfdaea460
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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