تفاعل #73853

معادلة التفاعل

tert-butyl 3-iodo-(1H)-pyrrolo[2,3-b]pyridine-1-carboxylate

trimethylsilylacetylene

triethylamine

benzyl azide

→

tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThen, for the removal of excess trimethylsilylacetylene, argon
2. 2
   workup.WAITis passed through the reaction mixture for 5 minutes
3. 3
   workup.ADDITION1.10 ml (1.10 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added
4. 4
   workup.STIRRINGthe reaction mixture is stirred at room temperature for 30 minutes
5. 5
   workup.STIRRINGthe reaction mixture is stirred at room temperature for 66 hours
6. 6
   أخرىchromatographed on a silica-gel column with petroleum ether/ethyl acetate 2:1

الإجراء التجريبي

1.1 0.21 ml (1.50 mmol) of trimethylsilylacetylene and 0.28 ml (2.00 mmol) of triethylamine are added successively to a suspension, kept under argon, of 14 mg (0.02 mmol) of bis(triphenylphosphine)palladium dichloride, 8 mg (0.04 mmol) of copper(I) iodide and 344 mg (1.00 mmol) of tert-butyl 3-iodo-(1H)-pyrrolo[2,3-b]pyridine-1-carboxylate in 5 ml of THF, and the mixture is stirred at room temperature for one hour under argon. Then, for the removal of excess trimethylsilylacetylene, argon is passed through the reaction mixture for 5 minutes. 1.10 ml (1.10 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are subsequently added, and the reaction mixture is stirred at room temperature for 30 minutes. A solution of 136 mg (1.00 mmol) of benzyl azide in 1 ml of THF is then added, and the reaction mixture is stirred at room temperature for 66 hours. The reaction mixture is adsorbed onto kieselguhr and chromatographed on a silica-gel column with petroleum ether/ethyl acetate 2:1, giving tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate as yellow oil; ESI 376.

المصدر