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

HRID 1617609Notes

Reaction equation

HRID 1617609 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])[CH2:9]/[C:10](/[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)=[N:11]\[OH:12])=[CH:4][CH:3]=1.[CH2:28]([O:30][C:31]([C:33]1[S:37][CH:36]=[C:35](B(O)O)[CH:34]=1)=[O:32])[CH3:29].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]>[CH2:28]([O:30][C:31]([C:33]1[S:37][CH:36]=[C:35]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[F:27])[CH2:9]/[C:10](=[N:11]\[OH:12])/[C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)=[CH:4][CH:3]=2)[CH:34]=1)=[O:32])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 44118617(5-(Ethoxycarbonyl)thiophen-3-yl)boronic acidHCID 136166969(NE)-N-[3-(4-bromophenyl)-3-(4-chloro-2-fluorophenyl)-1-(2-methyl-4-pyridinyl)propylidene]hydroxylamine

Product 1

HCID 136167036ethyl 4-[4-[(3E)-1-(4-chloro-2-fluorophenyl)-3-hydroxyimino-3-(2-methyl-4-pyridinyl)propyl]phenyl]thiophene-2-carboxylate

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

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]+.

Sources & evidence

ORD record
ord-36d93f94f4d64a21b094d9e1150b473e
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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