Reaction #73855

Reaction equation

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

trimethylsilylacetylene

triethylamine

1-chloro-4-(chloromethyl)benzene

caesium azide

→

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

Solvents

methanol

methanol

THF

Conditions

Workup

1. 1
   OtherThen, for the removal of excess trimethylsilylacetylene, argon
2. 2
   workup.WAITis passed through the reaction mixture for 5 minutes
3. 3
   workup.ADDITION2.00 ml (2.0 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 51 hours
6. 6
   Otherchromatographed on a silica-gel column with petroleum ether/ethyl acetate 2:1

Procedure

2.1 0.43 ml (3.00 mmol) of trimethylsilylacetylene and 0.55 ml (4.00 mmol) of triethylamine are added successively to a suspension, kept under argon, of 28 mg (0.04 mmol) of bis(triphenylphosphine)palladium dichloride, 16 mg (0.08 mmol) of copper(I) iodide and 688 mg (2.00 mmol) of tert-butyl 3-iodo-(1H)-pyrrolo[2,3-b]pyridine-1-carboxylate in 10 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. 2.00 ml (2.0 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 322 mg (2.00 mmol) of 1-chloro-4-(chloromethyl)benzene in 5 ml of methanol, 350 mg (2.00 mmol) of caesium azide and 5 ml of methanol is then added, and the reaction mixture is stirred at room temperature for 51 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-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl]pyrrolo[2,3-b]pyridine-1-carboxylate as pale-yellow solid; ESI 410.

Source