Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | Ethyl 6-amino-5-bromonicotinate | HCID 7210833 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 67263320 | HCID 67263320 | 77% |
Reaction Steps
A mixture of ethyl 6-amino-5-bromonicotinate (245 mg, 1 mmol), phenylacetylene (220 mg, 2.2 mmol), (dppf)PdCl2 (40 mg), CuI (15 mg), toluene (2 mL), tetrahydrofuran (1 mL) and triethylamine (1 mL) was stirred at 80° C. under argon for 2 h. After cooling to RT, the mixture was washed with water, dried and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with ethyl acetate in heptanes (1:1) to provide ethyl 6-amino-5-(2-phenylethynyl)nicotinate (205 mg, 77%) as a solid. LC/MS; (M+H)+=267.2
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08148361B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-155f2ab6f82e47c9aa2948d502e9a9bf |
|---|
| Source note | uspto-grants-2012_04 |
|---|
