HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 178435594, compound → HCID 178525130, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | HCID 178435594 | HCID 178435594 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178525130 | HCID 178525130 | 39% |
Reaction Steps
To a stirring solution of (S)-2-(5-ethynyl-1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester (26 mg, 0.0723 mmol), CuI (3 mg) and bis(triphenylphosphine)palladium (II) dichloride (8 mg) in THF (1.5 mL) is added TEA (30 μL, 3.4 mmol). The reaction mixture is stirred at room temperature for 12 hours and filtered through celite and the filtrate is concentrated in vacuum to dryness. The residue is purified by flash column chromatography on silica gel (EtOAc/hexanes 0% to 100%) to give the title compound (S)-2-(5-{4-[2-((S)-1-benzyloxycarbonyl-piperidin-2-yl)-1H-benzoimidazol-5-yl]-buta-1,3-diynyl}-1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester (10 mg, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08354419B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-8cdc8b52bb134b70a7905f82927f403b |
| Source note | uspto-grants-2013_01 |