Pyridine → HCID 86634691, Verbindung

HRID 1404254

Reaktionsgleichung

Reaktionsgleichung von HRID 1404254
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3]1.B(O)(O)[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[N:11][CH:10]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Br:15][C:12]1[N:11]=[CH:10][C:9]([NH:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 1372541-Methyl-3-aminopyrazoleHCID 27627062-Bromopyridine-5-boronic acid

Produkt 1

HCID 86634691HCID 86634691, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-methyl-1H-pyrazol-3-ylamine (0.23 g, 2.3 mmol, 1.0 equiv) and 2-bromopyridyl-5-boronic acid (0.70 g, 3.5 mmol, 1.5 equiv) in 10 Ml dichloromethane was added pyridine (0.43 Ml, 5.4 mmol, 2.4 equiv), copper (II) acetate (0.63 g, 3.5 mmol, 1.5 equiv) and 4 Å molecular sieves. The heterogeneous reaction mixture was allowed to stir vigorously open to air overnight. The reaction was then filtered through Celite, concentrated in vacuo, and purified by silica gel chromatography to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.80 (s, 3 H) 5.84 (s, 1 H) 7.45 (d, J=8.59 Hz, 1 H) 7.60 (d, J=2.02 Hz,1 H) 7.86 (dd, J=8.59, 3.03 Hz, 1 H) 8.41 (d, J=2.78 Hz, 1 H) 8.92 (s, 1. H); (M+H)+ 255.1.

Aufarbeitung

  1. filtrationThe reaction was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bf5ce37bd8454c5f8094c8b1e360c72a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912208B2

Verknüpfte Notizen

Wird geladen…