Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | 2-Pyridinecarboxamide, 5-bromo-N-(1,1-dimethylethyl)- | HCID 10999696 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66571174 | HCID 66571174 | 70% |
Reaction Steps
Bis-(triphenylphosphine)-palladium(II)dichloride (31 mg, 44.7 μmol, 0.05 equiv.) was dissolved in 2 ml DMF. (230 mg, 894 μmol) 5-Bromo-pyridine-2-carboxylic acid tert-butylamide (Example 1, step 1) and phenylacetylene (183 mg, 196 μl, 1.79 mmol, 2 equiv.) were added at room temperature. Triethylamine (272 mg, 374 μl, 2.68 mmol, 3 equiv.), triphenylphosphine (7 mg, 26.8 μmol, 0.03 equiv.) and copper(I)iodide (5 mg, 26.8 μmol, 0.03 equiv.) were added and the mixture was stirred for 2 hours at 70° C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column eluting with an ethyl acetate:heptane gradient 0:100 to 100:0. The desired 5-phenylethynyl-pyridine-2-carboxylic acid tert-butylamide (174 mg, 70% yield) was obtained as a light yellow solid, MS: m/e=279.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08772300B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-2e3c44188aa0434783676750b4dda6a9 |
|---|
| Source note | uspto-grants-2014_07 |
|---|
