반응 #73857

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tert-butyl 3-iodo-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

trimethylsilylacetylene

triethylamine

benzyl azide

→

tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate

용매

THF

methanol

반응 조건

후처리

1. 1
   기타Then, for the removal of excess trimethylsilylacetylene, argon
2. 2
   workup.WAITis passed through the reaction mixture for 5 minutes
3. 3
   workup.ADDITION0.45 ml (0.45 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 48 hours
6. 6
   기타chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent

실험 절차

3.4 0.09 ml (0.63 mmol) of trimethylsilylacetylene and 0.12 ml (0.84 mmol) of triethylamine are added successively to a suspension, kept under argon, of 6 mg (0.009 mmol) of bis(triphenylphosphine)palladium dichloride, 3 mg (0.016 mmol) of copper(I) iodide and 178 mg (0.42 mmol) of tert-butyl 3-iodo-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate in 2 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. 0.45 ml (0.45 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 58 mg (0.42 mmol) of benzyl azide in 2 ml of methanol is then added, and the reaction mixture is stirred at room temperature for 48 hours. The reaction mixture is adsorbed onto kieselguhr and chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent, giving tert-butyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,3-b]pyridine-1-carboxylate as colourless crystals; ESI 456.

출처