Pyridine → 1-(4-Fluorophenyl)-5-iodo-6-methylindazole

HRID 1098831

Reaktionsgleichung

Reaktionsgleichung von HRID 1098831
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][N:6]=[CH:5]2.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([I:1])=[C:10]([CH3:11])[CH:9]=3)[CH:5]=[N:6]2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 1049Pyridine2×HCID 2856454-Fluorophenylboronic acid2×HCID 593396965-iodo-6-methyl-1H-indazole

Produkt 1

HCID 593399141-(4-Fluorophenyl)-5-iodo-6-methylindazoleAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Iodo-6-methylindazole (1.3 g, 5.0 mmol), p-fluorobenzeneboronic acid (1.4 g, 10 mmol), anhydrous copper(II) acetate (1.4 g, 7.5 mmol) and pyridine (0.80 mL, 10 mmol) were stirred in dichloromethane (30 mL) overnight. Additional portions of p-fluorobenzeneboronic acid (0.47 g, 3.4 mmol), anhydrous copper(II) acetate (0.45 g, 2.5 mmol) and pyridine (0.27 mL, 3.4 mmol) were added. The mixture was filtered through celite after stirring for an additional night. The filtrate was concentrated and purified by column chromatography (SiO2, toluene) to give the subtitle compound (0.90 g, 51%) as a light orange powder.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography (SiO2, toluene)

Quellen und Nachweise

ORD-Eintrag
ord-2ddaf770e336452fa64a04bd6a684a14
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

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