Water → ethyl 4-[4-[(3E)-1-(4-chloro-2-fluorophenyl)-3-hydroxyimino-3-(2-methyl-4-pyridinyl)propyl]phenyl]thiophene-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(5-(Ethoxycarbonyl)thiophen-3-yl)boronic acid	HCID 44118617	—
Reactant	(NE)-N-[3-(4-bromophenyl)-3-(4-chloro-2-fluorophenyl)-1-(2-methyl-4-pyridinyl)propylidene]hydroxylamine	HCID 136166969	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 44119782	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	ethyl 4-[4-[(3E)-1-(4-chloro-2-fluorophenyl)-3-hydroxyimino-3-(2-methyl-4-pyridinyl)propyl]phenyl]thiophene-2-carboxylate	HCID 136167036	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

In analogy to example 74, step 6, (E)-3-(4-bromo-phenyl)-3-(4-chloro-2-fluoro-phenyl)-1-(2-methyl-pyridin-4-yl)-propan-1-one oxime (example 147, step 5) was reacted with 5-(ethoxycarbonyl)thiophen-3-ylboronic 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 under heating by microwave irradiation to 100° C. for 30 min providing the title compound as an off-white solid, MS (ESI+): m/z=523.2 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765730B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-36d93f94f4d64a21b094d9e1150b473e
Source note	uspto-grants-2014_07