Bromobenzene → 6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-1-methyl-N-phenyl-1H-indazol-3-amine

HRID 1865209

Reaktionsgleichung

CC(C)([O-])C.[Na+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[O:21][C:22]1[CH:30]=[C:29]2[C:25]([C:26]([NH2:32])=[N:27][N:28]2[CH3:31])=[CH:24][CH:23]=1.Br[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[O:21][C:22]1[CH:30]=[C:29]2[C:25]([C:26]([NH:32][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:27][N:28]2[CH3:31])=[CH:24][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A solution/suspension of Pd2dba3 (9.30 mg, 0.01 mmol), 2-(dicyclohexylphosphino)-2′-4′-6′-tri-i-propyl-1,1′-biphenyl (19.5 mg, 0.04 mmol), sodium tert-butoxide (46.0 mg, 0.48 mmol), 6-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine (Example 120, 119 mg, 0.34 mmol) and bromobenzene (53.4 mg, 0.34 mmol) in toluene (1 mL) was stirred at 100° C. for 16 h. After cooling to RT, the mixture was purified by silica gel chromatography (DCM/acetone: 100/0 to 70/30) to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 427.3 (M+1). Mass Calc'd for C25H22N4O3: 426.47.

Aufarbeitung

temperatureAfter cooling to RT
customthe mixture was purified by silica gel chromatography (DCM/acetone: 100/0 to 70/30)

Quellen und Nachweise

ORD-Eintrag: ord-d6d4a82e715440a9875e2121cc6e2a56
Quelldatensatz: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07626030B2

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