HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 57961596, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzenamine, 3-ethynyl- | HCID 104682 | — |
| Reactant | tert-Butyl (2-iodopyridin-4-yl)carbamate | HCID 24229174 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57961596 | HCID 57961596 | 89% |
Reaction Steps
tert-Butyl (2-iodopyridin-4-yl)carbamate (2.41 g, 7.5 mmol), copper(I) iodide (50 mg, 0.3 mmol) and bis(triphenylphosphine)palladium(II) chloride (200 mg, 0.3 mmol) were stirred in tetrahydrofuran (22 mL) with triethylamine (1.1 mL, 8.1 mmol) under N2 at rt. 3-Ethynylaniline (0.75 mL, 7.2 mmol) was added and the mixture was stirred at rt for 40 hours. The reaction mixture was diluted with water. After removal of the solvent, the aqueous residue was extracted with EtOAc three times, followed by drying, filtration, and concentration to give the desired product as a brown solid (1.97 g, 89%). LCMS for C18H20N3O2 (M+H)+: m/z=310.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08871753B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-e8db9e7fb8414773aa4185cfde478a14 |
| Source note | uspto-grants-2014_10 |