Reacción #822012

Ecuación de reacción

EtOAc

triethylamine

methyl 5-iodobenzo[b]thiophen-2-carboxylate

5-(4-chlorophenyl)-2-ethynylpyridine

→

methyl 5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]benzo[b]thiophen-2-carboxylate

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction mixture was evacuated three times
2. 2
   Filtraciónthe precipitated product was filtered off
3. 3
   Lavadowashed with a little EtOAc
4. 4
   Otrodried in the air
5. 5
   Otro7.3 minutes (method B)

Procedimiento

Under an argon atmosphere 3.7 mL (26.72 mmol) of triethylamine was added to a solution of 3.4 g (10.69 mmol) of methyl 5-iodobenzo[b]thiophen-2-carboxylate and 2.48 g (10.69 mmol) of 5-(4-chlorophenyl)-2-ethynylpyridine in 20 mL of THF and the reaction mixture was evacuated three times and in each case gassed with argon. Then 195 mg (0.267 mmol) of PdCl2(dppf)*DCM complex and 51 mg (0.267 mmol) of CuI were added and the reaction mixture was stirred for 70 hours at RT. EtOAc was added, and the precipitated product was filtered off, washed with a little EtOAc, and dried in the air. Yield: 3.0 g (70% of theoretical); C23H14ClNO2S (M=403.881); calc.: molpeak (M+H)+: 404/406 (Cl); found: molpeak (M+H)+: 404/406 (Cl); HPLC-MS: 7.3 minutes (method B).

Fuente