Sodium Carbonate → 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-3H-imidazo[4,5-c]pyridine

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Reaktionsgleichung

Br[C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9]([C:11]3[N:12]([CH3:20])[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=3)=[N:10][C:4]=2[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[C:16]([C:14]1[CH:15]=[C:11]([C:9]2[NH:8][C:5]3[CH:6]=[N:7][C:2]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[Cl:21])=[CH:3][C:4]=3[N:10]=2)[N:12]([CH3:20])[N:13]=1)([CH3:19])([CH3:18])[CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A solution of 6-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine (50 mg, 0.15 mmol, prepared as described in the previous step), 2-chlorophenylboronic acid (47 mg, 0.30 mmol), 2M Na2CO3 (0.60 mL, 1.2 mmol) and DME (1 mL) was stirred at 90° C. for 18 h. The resulting mixture was allowed to cool to room temperature and organic layer was separated. The organic layer was purified by direct application to silica preparative TLC plates (2000 micron) and eluted with 3:7 EtOAc-hexanes to yield 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-3H-imidazo[4,5-c]pyridine.

Aufarbeitung

temperatureto cool to room temperature
customorganic layer was separated
customThe organic layer was purified by direct application to silica preparative TLC plates (2000 micron)
washeluted with 3:7 EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag: ord-a6407f50280d4fe2bdb81062da263b72
Quelldatensatz: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08680098B2

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