Pyridine → 4-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole-6-carbonitrile

HRID 2423065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423065
[Br:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[F:30])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:22]([F:30])[CH:23]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 247289174-Bromo-1H-indazole-6-carbonitrile

Produkt 1

HCID 672446504-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole-6-carbonitrileAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-1H-indazole-6-carbonitrile (1.0 g, 4.50 mmol) in dichloromethane (80 mL) was added 4-benzyloxy-3-fluorobenzeneboronic acid (2.2 g, 8.94 mmol), pyridine (0.71 mL, 8.78 mmol), copper acetate (1.2 g, 6.63 mmol) and powdered 4A molecular sieves (2.0 g). The reaction mixture was stirred at room temperature in the presence of air for 6 days. Celite was added to the mixture then the mixture was filtered through a pad of celite and then the filtrate concentrated in vacuo. The product was purified by silica gel chromatography eluting with 5-100% dichloromethane in hexane to yield the title compound (D5) (774 mg).

Aufarbeitung

  1. additionCelite was added to the mixture
  2. filtrationthe mixture was filtered through a pad of celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe product was purified by silica gel chromatography
  5. washeluting with 5-100% dichloromethane in hexane

Quellen und Nachweise

ORD-Eintrag
ord-76b0cd1995504074816d4eaaf6399448
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960563B2

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