Reaktion #166232

Reaktionsgleichung

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

O-(2-vinyloxy-ethyl)-hydroxylamine

EDCI

HOBt

DIPEA

→

title compound

Ausbeute 71.2%

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

Ausbeute 71.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenbefore being concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe resultant residue was dissolved in ethyl acetate (30 mL)
3. 3
   Waschenwashed with aqueous saturated sodium hydrogen carbonate solution (300 mL)
4. 4
   Extraktionthe aqueous fraction extracted with ethyl acetate (2×20 mL)
5. 5
   WaschenThe combined organic extracts were washed with brine (30 mL)
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated in vacuo

Vorschrift

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.

Quelle