Reacción #8595

Ecuación de reacción

water

triethylamine

2-(6-chloro-2-pyridinyl)-1-(methoxyphenyl)ethanone oxime

trifluoroacetic anhydride

→

7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridine

Rendimiento 52.0%

Disolventes

1,2-dimethoxyethane

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe temperature below 10° C.
2. 2
   workup.ADDITIONduring the addition
3. 3
   workup.ADDITIONAfter the addition
4. 4
   TemperaturaThe solution was then cooled to 4° C.
5. 5
   Temperaturato warm to room temperature
6. 6
   Temperaturathe reaction was heated at 75° C. for 15 hours
7. 7
   ExtracciónThe resulting suspension was extracted with ethyl acetate
8. 8
   SecadoThe organic phase was dried (magnesium sulfate)
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated to a solid
11. 11
    OtroThis solid was recrystallized from methanol

Procedimiento

To a solution of 2-(6-chloro-2-pyridinyl)-1-(methoxyphenyl)ethanone oxime (38.7 g, 140 mmol) in 1,2-dimethoxyethane (156 mL) at 0° C. was added trifluoroacetic anhydride (20 mL, 140 mmol), keeping the temperature below 10° C. during the addition. After the addition was complete, the reaction was warmed to 15° C. The solution was then cooled to 4° C. and a solution of triethylamine (39 mL, 280 mmol) in 1,2-dimethoxyethane (15 mL) was added over a period of 0.5 hours. The mixture was allowed to warm to room temperature and was stirred at room temperature for 1.5 hours. To this mixture was added iron(II) chloride (0.18 g, 1.4 mmol) and the reaction was heated at 75° C. for 15 hours. The reaction mixture was poured into water (300 mL). The resulting suspension was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated to a solid. This solid was recrystallized from methanol to give 7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridine (18.7 g, 52%) as pale yellow needles. 1H NMR (CDCl3): δ 7.91 (d, 2H), 7.43 (d, 1H), 7.01 (t,1H), 6.95 (d, 2H). 6.81 (d,1 1H), 6.80 (s, 1H), 3.83 (s, 3 H); MS m/z 259 (M+1).

Fuente