Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | HCID 25258089 | HCID 25258089 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 25258327 | HCID 25258327 | 70% |
Reaction Steps
A solution (0.1 M) of ethyl 5-bromo-4-[(tert-butoxycarbonyl)amino]thiophene-2-carboxylate in THF was treated with trimethylsilylacetylene (1.3 eq.), Et3N (1.5 eq.), CuI (0.04 eq.) and PdCl2(PPh3)2 (0.01 eq.). The solution was heated at 50° C. for 3 h. After cooling down, it was filtered through a pad of celite and washed with AcOEt. The organic layer was washed with brine and dried then concentrated and the residue was purified by flash chromatography on silica gel (1:19 AcOEt/petroleum ether) to afford the title compound (70%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07781431B2 |
|---|
| Source dataset | uspto-grants-2010_08 |
|---|
| ORD ID | ord-66d6c5e0b11b415faad8faf8bb432bd5 |
|---|
| Source note | uspto-grants-2010_08 |
|---|
