Reaktion #88089

Reaktionsgleichung

4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester

iodobenzene

(1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine

Cs2CO3

→

4-(5-Methyl-pyridin-2-yl)-1-phenyl-1H-indazole-6-carboxylic acid methyl ester

Ausbeute 53.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Sonstigepartitioned between water and ethyl acetate
3. 3
   SonstigeThe organic layer was separated
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigePurification of the residue by column chromatography

Vorschrift

To a solution of 4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester (0.183 g, 0.684 mmol) in DMF (5 mL) was added iodobenzene (0.15 g, 0.753 mmol), CuI (0.028 g, 0.137 mmol), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (0.04 g, 0.274 mmol), and Cs2CO3 (0.15 g, 1.36 mmol). The reaction mixture was stirred at 110° C. overnight, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography gave 0.12 g (53%) of 4-(5-Methyl-pyridin-2-yl)-1-phenyl-1H-indazole-6-carboxylic acid methyl ester.

Quelle