Potassium Carbonate → HCID 73296271, Verbindung

HRID 524344

Reaktionsgleichung

[CH3:1][S:2]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17](Br)=[C:16]([CH3:21])[N:15]([CH:22]([CH3:24])[CH3:23])[CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[CH:31][N:30]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][S:2]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17]([C:33]3[CH:32]=[CH:31][N:30]=[C:29]([C:28]([F:39])([F:38])[F:27])[CH:34]=3)=[C:16]([CH3:21])[N:15]([CH:22]([CH3:24])[CH3:23])[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-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (preparation 5, 24 mg, 0.054 mmol), 2-(trifluoromethyl)pyridine-4-boronic acid (13 mg, 0.068 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5 mg, 0.007 mmol) in acetonitrile (0.15 mL) is added 2 M aqueous K2CO3 solution (0.055 mL, 0.11 mmol). After stirring for 18 h at 75° C., the reaction mixture is filtered and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 4 mg (15% of theory); ESI mass spectrum: [M+H]+=508; Retention time HPLC: 0.88 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.)
custom0.88 min (Z003_001)

Quellen und Nachweise

ORD-Eintrag: ord-310879f39c7440c39cc8a647db580f9c
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09340507B2

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