[4-(Methoxycarbonyl)-2-methylphenyl]boronic acid → HCID 89782937, Verbindung

HRID 58065

Reaktionsgleichung

Reaktionsgleichung von HRID 58065
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]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[C:21]([CH3:28])[CH:20]=1)=[O:18]>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]>[CH3:28][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][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)[C:17]([O:16][CH3:15])=[O:18]

Komponenten

6

Edukt 2

HCID 22171419[4-(Methoxycarbonyl)-2-methylphenyl]boronic acidHCID 247292324-Bromo-6-(trifluoromethyl)-1H-indazole

Produkt 1

HCID 89782937HCID 89782937, Verbindung

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

To a microwave vial was added a mixture 4-bromo-6-(trifluoromethyl)-1H-indazole (0.478 g, 1.804 mmol), (4-(methoxycarbonyl)-2-methylphenyl)boronic acid (0.35 g, 1.804 mmol) and PdCl2(dppf) (0.066 g, 0.090 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light yellow suspension was heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the residue was diluted with EtOAc and washed with water. The volatiles were removed via rotary evaporation to give the title compound, which was used without further purification (0.53 g). ESI-MS m/z [M+H]+ calc'd for C17H13F3N2O2, 335.1. found 335.2.

Aufarbeitung

  1. concentrationThe reaction mixture was subsequently concentrated
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water
  4. customThe volatiles were removed via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-baa272f5ec214d7b956cc5f094773292
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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