Reaktion #60322

Reaktionsgleichung

Ethynyl-trimethylsilane

7-Fluoro-6-(4-iodo-2-methyl-phenylamino)-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

→

desired product

Ausbeute 87.0%

7-Fluoro-6-(2-methyl-4-trimethylsilanylethynyl-phenylamino)-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

Ausbeute 87.0%

Lösungsmittel

acetonitrile triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is cooled to room temperature
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigeThe residue is purified by FCC (eluting with 20:1 methylene chloride:methanol)

Vorschrift

7-Fluoro-6-(4-iodo-2-methyl-phenylamino)-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide 11ccc (0.025 g, 0.052 mmol) is dissolved in 1:1 acetonitrile/triethylamine (0.50 mL). Ethynyl-trimethylsilane (0.013 mL, 0.092 mmol), Pd(PPh3)2Cl2 (0.004 g, 0.006 mmol), and CuI (0.002 g, 0.011 mmol) are added consecutively and the reaction mixture is stirred at 60° C. for 1 hour under N2. The reaction mixture is cooled to room temperature and concentrated under reduced pressure. The residue is purified by FCC (eluting with 20:1 methylene chloride:methanol) to yield 0.020 g (87%) of the desired product.

Quelle