Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methyl 5-iodo-1-benzothiophene-2-carboxylate | HCID 19007488 | — |
| Reactant | 5-(4-Chloro-phenyl)-2-ethynyl-pyridine | HCID 57845328 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 69058356 | HCID 69058356 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07592358B2 |
|---|
| Source dataset | uspto-grants-2009_09 |
|---|
| ORD ID | ord-b61885f642e54f378a06c87d5236a8e0 |
|---|
| Source note | uspto-grants-2009_09 |
|---|
