Potassium Carbonate → HCID 86729306, Verbindung

HRID 1399919

Reaktionsgleichung

Reaktionsgleichung von HRID 1399919
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH3:10])[C:6]=2[CH:11]=1.[NH2:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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]>[CH3:10][N:7]1[C:6]2[CH:11]=[C:2]([C:17]3[CH:18]=[C:13]([CH:14]=[CH:15][CH:16]=3)[NH2:12])[CH:3]=[CH:4][C:5]=2[N:9]=[CH:8]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 235376446-Bromo-1-methyl-1H-benzimidazole

Produkt 1

HCID 86729306HCID 86729306, VerbindungAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 6-bromo-1-methyl-1H-benzo[d]imidazole (500 mg, 2.37 mmol) in dioxane (10 mL) was added (3-aminophenyl)boronic acid (320 mg, 2.34 mmol), 2N K2CO3 (2 mL, 4 mmol) and PdCl2(dppf) (50 mg, 0.063 mmol). The reaction mixture was heated at 120° C. under microwave conditions for 30 min. The cooled mixture was concentrated under reduced pressure and the residue dissolved in ethyl acetate, washed with water with the separated organic layers being dried and concentrated to afford the desired product as a brown solid (300 mg, 56.7%). LCMS (m/z): 224.1 [M+H]+

Aufarbeitung

  1. concentrationThe cooled mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water with the separated organic layers
  4. custombeing dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c6cff7fe2468448da96a3bb940e1fbf7
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906900B2

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