(3-Acetamidophenyl)boronic acid → HCID 67015613, compound

HRID 1617876Notes

Reaction equation

HRID 1617876 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.[C:21]([NH:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)(=[O:23])[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:30]=[C:25]([NH:24][C:21](=[O:23])[CH3:22])[CH:26]=[CH:27][CH:28]=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 157274(3-Acetamidophenyl)boronic acidHCID 516892Sodium BicarbonateHCID 66668501HCID 66668501, compound

Product 1

HCID 67015613HCID 67015613, 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-methylpyridin-2(1H)-one (example 319, step 2) was reacted with 3-acetamidophenylboronic 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 brown solid, MS (ESI+): m/z=427.1 [M+H]+.

Sources & evidence

ORD record
ord-f9a6d3854ff34db58e64032dc57dcc47
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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