Réaction #60260

Équation de réaction

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid

O-(2-vinyloxy-ethyl)-hydroxylamine

HOBt

triethylamine

EDCI

→

desired product

Rendement 90.1%

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-vinyloxy-ethoxy)-amide

Rendement 90.1%

Solvants

ethyl acetate

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (3×), saturated potassium carbonate (2×), saturated ammonium chloride (2×), brine
2. 2
   Séchagedried (Na2SO4)
3. 3
   Concentrationconcentrated under reduced pressure to an off-white solid

Mode opératoire

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid 10c (2.00 g, 5.0 mmol), O-(2-vinyloxy-ethyl)-hydroxylamine (0.776 g, 7.5 mmol), HOBt (0.88 g, 6.5 mmol), triethylamine (1.61 mL, 2.3 mmol) and EDCI (1.3 g, 6.5 mmol) are dissolved in dimethylformamide (52 mL) and stirred at room temperature for 48 hours. The reaction mixture is diluted with ethyl acetate, washed with water (3×), saturated potassium carbonate (2×), saturated ammonium chloride (2×), brine, dried (Na2SO4) and concentrated under reduced pressure to an off-white solid. Trituration of the solid with diethyl ether provides 2.18 g (90%) desired product as an off-white solid. MS ESI (+) m/z 483, 485 (M+Br pattern) detected.

Source