Water → 3-[4-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]phenyl]benzoic acid

HRID 1617697Notes

Reaction equation

HRID 1617697 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:9]/[C:10](/[C:13]2[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)=[N:11]\[OH:12])=[CH:4][CH:3]=1.[C:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)([OH:30])=[O:29].O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.Cl[Pd]Cl.[Fe+2]>[OH:12]/[N:11]=[C:10](/[C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)\[CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([C:28]([OH:30])=[O:29])[CH:32]=2)=[CH:3][CH:4]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 580434145-[(E)-C-[2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Product 1

HCID 580436093-[4-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]phenyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

In analogy to example 166, step 1, 5-{3-(4-bromo-phenyl)-1-[(E)-hydroxyimino]-3-o-tolyl-propyl}-1-methyl-1H-pyridin-2-one (example 162, step 4) was reacted with 3-carboxyphenylboronic acid in the presence of dichloro(1,1′-bis(diphenylphosphino)ferrocene)-palladium(II) dichloromethane adduct in a mixture of 1,4-dioxane, water and 2 M aqueous sodium carbonate solution to give the title compound as a light yellow foam, MS (ESI−): m/z=465.1 [M−H]−.

Sources & evidence

ORD record
ord-1844a96cada74484b71d7e11622f0a7a
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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