Réaction #166232

Équation de réaction

4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid

O-(2-vinyloxy-ethyl)-hydroxylamine

EDCI

HOBt

DIPEA

→

title compound

Rendement 71.2%

4-(2-Fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (2-vinyloxyethoxy)-amide

Rendement 71.2%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Concentrationbefore being concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe resultant residue was dissolved in ethyl acetate (30 mL)
3. 3
   Lavagewashed with aqueous saturated sodium hydrogen carbonate solution (300 mL)
4. 4
   Extractionthe aqueous fraction extracted with ethyl acetate (2×20 mL)
5. 5
   LavageThe combined organic extracts were washed with brine (30 mL)
6. 6
   Séchagedried (MgSO4)
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (2.14 g, 5.39 mmol) and O-(2-vinyloxy-ethyl)-hydroxylamine (668 mg, 6.50 mmol) in DMF (50 mL) was added EDCI (1.14 g, 5.93 mmol), HOBt (0.80 g, 5.93 mmol) and DIPEA (1 mL, 5.93 mmol). The reaction mixture was stirred at room temperature for 2 hours before being concentrated in vacuo. The resultant residue was dissolved in ethyl acetate (30 mL), washed with aqueous saturated sodium hydrogen carbonate solution (300 mL) and the aqueous fraction extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-100% ethyl acetate in cyclohexane) to yield the title compound as a pale yellow solid (1.85 g, 71%). LCMS (Method B): RT=3.52 min, [M−H]−=481.

Source