HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 59424500, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-(2-Propyn-1-yl)morpholine | HCID 412941 | — |
| Reactant | 2-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine | HCID 59424521 | — |
| 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 59424500 | HCID 59424500 | 79% |
Reaction Steps
To a solution of bromide 42 (100 mg, 0.27 mmol) in THF (5 ml) was added 4-(prop-2-ynyl)morpholine (68 mg, 0.54 mmol) [H-W. Tsou, et. al. J. Med. Chem., 2001, 44, 2719-2734], triethylamine (68 mg, 0.67 mmol), CuI (5 mg, 0.03 mmol) and Pd(PPh3)2Cl2 (5.3 mg, 7.56 μmol. The reaction mixture was degassed with nitrogen and refluxed for 2 hrs, cooled to room temperature and adsorbed onto silica. Purification by column chromatography (eluent EtOAc) afforded the title compound 56 as a beige solid (88 mg, 79%). MS (m/z): 397.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08470850B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-05bf6e509e0f4e249906b0fe77b353ab |
| Source note | uspto-grants-2013_06 |