4-Bromo-6-(trifluoromethyl)-1H-indazole → HCID 89782890, Verbindung

HRID 58063

Reaktionsgleichung

Reaktionsgleichung von HRID 58063
Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1>O1CCOCC1.C([O-])(O)=O.[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]>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:21][C:22]=1[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Komponenten

6

Edukt 2

HCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazoleHCID 57576289Methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetate

Produkt 1

HCID 89782890HCID 89782890, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.433 g, 1.633 mmol), methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (0.5 g, 1.633 mmol) and PdCl2(dppf) (0.060 g, 0.082 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated. The crude residue was dissolved in EtOAc and was washed with water and brine, concentrated, and purified by CombiFlash® chromatography (0-35% MeOH in DCM). The product-containing fractions were combined and concentrated by rotary evaporation to give the title compound (0.47 g, 79%). ESI-MS m/z [M+H]+ calc'd for C18H15F3N2O3, 365.1. found 365.2.

Aufarbeitung

  1. concentrationThe reaction mixture was subsequently concentrated
  2. dissolutionThe crude residue was dissolved in EtOAc
  3. washwas washed with water and brine
  4. concentrationconcentrated
  5. custompurified by CombiFlash® chromatography (0-35% MeOH in DCM)
  6. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-edf0eb21465345309be40b2e3200d4f8
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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