تفاعل #333449

معادلة التفاعل

2-(6-fluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

4-(2-chloroacetyl)morpholine

cesium carbonate

→

2-[6-fluoro-1-(2-morpholin-4-yl-2-oxo-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

المردود 68.2%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe vial was flushed with argon
2. 2
   أخرىsealed
3. 3
   أخرىThe reaction mixture was quenched with water
4. 4
   استخلاصextracted with diethyl ether (2×)
5. 5
   غسيلThe organic layers were washed twice with water and once with brine
6. 6
   تجفيفthen dried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-70% EtOAc)

الإجراء التجريبي

A 5 ml microwave vial was charged with 2-(6-fluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (300 mg, 0.73 mmol), 4-(2-chloroacetyl)morpholine (0.19 ml, 1.46 mmol), cesium carbonate (713 mg, 2.19 mmol) and DMF (3.3 ml). The vial was flushed with argon, sealed and heated in a microwave reactor at 100° C. for 2 h. The reaction mixture was quenched with water and extracted with diethyl ether (2×). The organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-70% EtOAc) to afford 268 mg (68%) of 2-[6-fluoro-1-(2-morpholin-4-yl-2-oxo-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as a yellow powder.

المصدر