Reacción #434700

Ecuación de reacción

sodium bicarbonate

phosphorus(III) oxychloride

5-chloropyrrolo[2,1-f][1,2,4]triazin-4 (3H)-one

diisopropylethylamine

→

crude product

Rendimiento 67.3%

4,5-Dichloropyrrolo[2,1-f][1,2,4]triazine

Rendimiento 67.3%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas then cooled to rt
2. 2
   workup.ADDITIONAfter the addition
3. 3
   ExtracciónThe aqueous phase was extracted with ethyl acetate (3×500 mL)
4. 4
   Secadodried over anhydrous MgSO4
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 5-chloropyrrolo[2,1-f][1,2,4]triazin-4 (3H)-one (5.00 g, 29.5 mmol) in toluene (100 mL) at rt under nitrogen was added diisopropylethylamine (5.14 mL, 29.5 mmol) followed by phosphorus(III) oxychloride (8.25 mL, 88.5 mmol). The mixture was heated at 100° C. for 20 h and was then cooled to rt. The reaction was slowly added to saturated aqueous sodium bicarbonate solution (500 mL) at 0° C. After the addition was complete, the mixture was stirred at rt for 30 min. The aqueous phase was extracted with ethyl acetate (3×500 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude product (3.73 g, 67%) as a yellow solid which was used without further purification. 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.70 (d, 1H, J=2.8 Hz), 6.84 (d, 1H, J=2.8 Hz); MS(ESI+) m/z 188.1 (M+H)+.

Fuente