Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzenamine, 3-ethynyl- | HCID 104682 | — |
| Reactant | tert-Butyl (6-iodopyridin-2-yl)carbamate | HCID 24229165 | — |
| 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 57962721 | HCID 57962721 | 89% |
Reaction Steps
tert-Butyl (6-iodopyridin-2-yl)carbamate (1.50 g, 4.68 mmol), copper(I) iodide (68.0 mg, 0.36 mmol) and bis(triphenylphosphine)palladium(II) chloride (100 mg, 0.2 mmol) were stirred in tetrahydrofuran (14 mL) with triethylamine (0.70 mL, 5.0 mmol) under N2 at rt. 3-Ethynylaniline (0.47 mL, 4.5 mmol) was added and the mixture was heated at 60° C. overnight. The mixture was filtered, washed with EtOAc and concentrated under vacuum to give the desired product as a brown solid (1.23 g, 89%). LCMS for C14H12N3O2 ([M-(tBu)+H]+H)+: m/z=254.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08871753B2 |
|---|
| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-c7665e420b864b4c8351c49d852881d7 |
|---|
| Source note | uspto-grants-2014_10 |
|---|
