6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indol-2-one → 6-(6-(3-(3-Fluorophenyl)morpholino)imidazo[1,2-b]pyridazin-3-yl)indolin-2-one

HRID 1890673Notizen

Reaktionsgleichung

Br[C:2]1[N:6]2[N:7]=[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH:12]3[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:40]=[C:39]3[C:35]([CH2:36][C:37](=[O:41])[NH:38]3)=[CH:34][CH:33]=2)O1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:23][C:19]1[CH:18]=[C:17]([CH:12]2[N:11]([C:8]3[CH:9]=[CH:10][C:5]4[N:6]([C:2]([C:32]5[CH:40]=[C:39]6[C:35]([CH2:36][C:37](=[O:41])[NH:38]6)=[CH:34][CH:33]=5)=[CH:3][N:4]=4)[N:7]=3)[CH2:16][CH2:15][O:14][CH2:13]2)[CH:22]=[CH:21][CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

In step 2-6, a suspension of 4-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-3-(3-fluorophenyl)morpholine (25 mg, 0.067 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (34 mg, 0.13 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.7 mg, 0.0033 mmol) in 3 mL of 1,4-dioxane and 0.5 mL of 2.0M sodium carbonate was bubbled with nitrogen and heated to 150° C. and stirred for 20 hours. The solution was cooled to room temperature and purified with HPLC to afford 6-(6-(3-(3-fluorophenyl)morpholino)imidazo[1,2-b]pyridazin-3-yl)indolin-2-one (2-6) as a white solid.

Aufarbeitung

customwas bubbled with nitrogen
temperatureThe solution was cooled to room temperature
custompurified with HPLC

Quellen und Nachweise

ORD-Eintrag: ord-61b1b3f61bce454a81173ef9510207b5
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08507488B2

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