Réaction #2204263

Équation de réaction

ethyl 3-chloro-3-oxopropanoate

3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

Compound C

3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

diisopropylethylamine

→

crude product

Ethyl 3-(3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenylamino)-3-oxopropanoate

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autrewas then quenched with 10 mL of saturate NaHCO3 solution
2. 2
   ExtractionThe aqueous layer was extracted with chloroform (3×15 mL)
3. 3
   SéchageThe combined organic extracts were dried over anhydrous Na2SO4
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of 3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine (112 mg, 0.459 mmol, Compound C of Example 22) in methylene chloride (4 mL) at 0° C. was added 96 μL (0.55 mmol) of diisopropylethylamine followed by 61 μL (0.48 mmol) of ethyl 3-chloro-3-oxopropanoate. The reaction was stirred at 0° C. for 1 h and was then quenched with 10 mL of saturate NaHCO3 solution. The aqueous layer was extracted with chloroform (3×15 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product as a yellow oil that solidified on standing (180 mg).

Source