Water → HCID 58043491, compound

HRID 1617689Notes

Reaction equation

HRID 1617689 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])=[C:4]([F:28])[CH:3]=1.[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[C:36]([O:38][CH3:39])=[O:37].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]>[CH3:39][O:38][C:36]([C:35]1[CH:34]=[CH:33][C:32]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[CH2:9]/[C:10](=[N:11]\[OH:12])/[C:13]3[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=3)=[C:4]([F:28])[CH:3]=2)=[CH:31][C:30]=1[F:29])=[O:37]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acidHCID 580432005-[(E)-C-[2-(4-bromo-2-fluorophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Product 1

HCID 58043491HCID 58043491, compound

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-2-fluoro-phenyl)-1-[(E)-hydroxyimino]-3-o-tolyl-propyl}-1-methyl-1H-pyridin-2-one (example 193, step 4) was reacted with 3-fluoro-4-methoxycarbonylphenylboronic 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 brown solid, MS (ESI+): m/z=517.4 [M+H]+.

Sources & evidence

ORD record
ord-d363f4c458664a6e81b9347bff80f54f
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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