Water → 6-(1H-Indol-4-yl)-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indazole

HRID 38875

Reaktionsgleichung

Reaktionsgleichung von HRID 38875
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2S(C2C=CC(C)=CC=2)(=O)=O)=[C:4]([C:21]2[O:22][C:23]([CH3:26])=[N:24][N:25]=2)[CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH:37]=[CH:38][NH:39]3)O1.O.C(=O)(O)[O-].[Na+]>O1CCOCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[NH:39]1[C:40]2[C:36](=[C:35]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][NH:8]4)=[C:4]([C:21]4[O:22][C:23]([CH3:26])=[N:24][N:25]=4)[CH:3]=3)[CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:38]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 666923736-Bromo-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole

Produkt 1

HCID 666956896-(1H-Indol-4-yl)-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indazoleAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178477754HCID 178477754, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

6-Bromo-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole (70 mg, 0.162 mmol) was dissolved in 1,4-dioxane (1.2 ml) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (47.1 mg, 0.194 mmol, available from Frontier Scientific Europe), 1,1-bis(diphenylphosphino)ferrocenedichloropalladium(II) (5.91 mg, 8.08 μmol), water (0.8 ml) and 2M aqueous sodium bicarbonate (0.242 ml, 0.485 mmol) were added. The reaction mixture was heated under microwave irradiation at 150° C. for 15 mins. The solution was loaded onto a silica cartridge (0.5 g) and eluted with methanol. The eluant was concentrated, the residue dissolved in methanol and absorbed onto Florisil. This was placed on top of a silica cartridge (10 g) and eluted with 25-50% ethyl acetate/cyclohexane. Appropriate fractions were evaporated to give the title compound as a yellow solid (27 mg).

Aufarbeitung

  1. washeluted with methanol
  2. concentrationThe eluant was concentrated
  3. dissolutionthe residue dissolved in methanol
  4. customabsorbed onto Florisil
  5. washeluted with 25-50% ethyl acetate/cyclohexane
  6. customAppropriate fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1b930954699d407e9a3d93c9d0fcf987
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524751B2

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