تفاعل #86930

معادلة التفاعل

lithium chloride

sodium carbonate

5-chloro-3-iodopyridin-2-amine

4-(triethylsilyl)but-3-yn-1-ol

→

2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

المردود 88.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   تركيزthe mixture was concentrated under reduced pressure
3. 3
   أخرىthe residue was partitioned between brine and ethyl acetate
4. 4
   أخرىAfter separation the organic layer
5. 5
   أخرىwas evaporated
6. 6
   أخرىthe residue was purified by flash chromatography on silica gel (eluent 7 to 80% of ethyl acetate in heptane)

الإجراء التجريبي

A mixture of 5-chloro-3-iodopyridin-2-amine (2 g; 7.86 mmol), 4-(triethylsilyl)but-3-yn-1-ol (4.35 g; 23.58 mmol); (1,1′-bis(diphenylphosphino)ferrocene)-dichloromethane (0.321 g; 0.393 mmol), lithium chloride (0.333 g; 7.86 mmol) and sodium carbonate (1.67 g; 15.72 mmol) in DMF (15 mL) was heated at 100° C. for approximately 20 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was partitioned between brine and ethyl acetate. After separation the organic layer was evaporated and the residue was purified by flash chromatography on silica gel (eluent 7 to 80% of ethyl acetate in heptane) to give 2.15 g (88%) of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol as a white solid.

المصدر