Sodium Carbonate → N-{6-[4-(Acetylamino)phenyl]-1H-indazol-4-yl}-2-pyridinecarboxamide

HRID 1695764

Reaktionsgleichung

Reaktionsgleichung von HRID 1695764
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])[CH:3]=1.[C:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.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]>[C:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][NH:8]3)=[C:4]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[O:13])[CH:3]=2)=[CH:26][CH:25]=1)(=[O:22])[CH3:21]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27346574-Acetamidophenylboronic acidHCID 58255852HCID 58255852, Verbindung

Produkt 1

HCID 44540128N-{6-[4-(Acetylamino)phenyl]-1H-indazol-4-yl}-2-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-(6-Bromo-1H-indazol-4-yl)-2-pyridinecarboxamide (70 mg, 0.22 mmol), [4-(acetylamino)phenyl]boronic acid (47 mg, 0.26 mmol), Pd(dppf)Cl2 (22 mg, 0.027 mmol) and 2 M sodium carbonate (aq) (0.328 ml, 0.656 mmol) in 1,4-dioxane (1.5 ml) and water (1.5 ml) were heated in a Biotage microwave at 150° C. for 30 mins. The reaction was washed through a silica cartridge eluting with MeOH. The solvent was removed in vacuo. The residue was purified by HPLC using the method described below to afford the title compound.

Aufarbeitung

  1. washThe reaction was washed through a silica cartridge
  2. washeluting with MeOH
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-68f4808c169241f297964125d7d8c8ee
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163743B2

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