Potassium Carbonate → 1-(4-Cyano-benzyl)-6-methyl-4-oxo-5-phenyl-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 512502

Reaktionsgleichung

[CH3:1][S:2]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17](Br)=[C:16]([CH3:21])[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][S:2]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:16]([CH3:21])[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

To a solution of 5-bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (preparation 8, 80 mg, 0.156 mmol), phenylboronic acid (27 mg, 0.22 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11 mg, 0.016 mmol) in acetonitrile (2 mL) is added 2 M aqueous K2CO3 solution (0.16 mL, 0.32 mmol). After stirring for 72 h at 75° C., the reaction mixture is filtered, basified with aqueous NH4OH solution and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 59 mg (74% of theory); ESI mass spectrum: [M+H]+=512; Retention time HPLC: 0.98 min (Z003—001).

Aufarbeitung

filtrationthe reaction mixture is filtered
custompurified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
custom0.98 min (Z003—001)

Quellen und Nachweise

ORD-Eintrag: ord-f697c8c5f9a64223a4719bd5cbbd3673
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09102624B2

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