Methyl iodide → HCID 58043345, compound

HRID 1617952Notes

Reaction equation

HRID 1617952 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([C:13]2[CH:14]=[CH:15][C:16](=O)[NH:17][CH:18]=2)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.IC.[C:22](=[O:25])([O-])[O-].[K+].[K+].[CH3:28][S:29]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)(=[O:31])=[O:30].C(=O)([O-])O.[Na+].Cl.[NH2:47][OH:48]>O1CCOCC1.O.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[Cl:8][C:6]1[CH:5]=[C:4]([CH:9]([C:35]2[CH:36]=[CH:37][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:33][CH:34]=2)[CH2:10]/[C:11](/[C:13]2[CH:14]=[CH:15][C:22](=[O:25])[N:17]([CH3:16])[CH:18]=2)=[N:47]\[OH:48])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

10

Reactant 6

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate2×HCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 66668301HCID 66668301, compound

Product 1

HCID 58043345HCID 58043345, 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 161, step 1, (E)-5-(3-(3,5-dichlorophenyl)acryloyl)pyridin-2(1H)-one was reacted with iodomethane in the presence of potassium carbonate. The product of this reaction was treated in analogy to example 203, step 1, with 4-(methylsulfonyl)phenylboronic acid in the presence of chloro(1,5-cyclooctadiene)rhodium(I) dimer and sodium hydrogen-carbonate in 1,4-dioxane and water at 60° C. The product of this reaction was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound containing less than 10% of the corresponding Z isomer as an off-white solid, MS (ESI+): m/z=479.1 [M+H]+.

Sources & evidence

ORD record
ord-d0ab665af0c04f6e92646a09cc42bd7c
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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