HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-Bromo-5-(prop-1-yn-1-yl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3,5-Dibromopyridine | HCID 69369 | — |
| Reactant | 1-(Trimethylsilyl)prop-1-yne | HCID 80363 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-Bromo-5-(prop-1-yn-1-yl)pyridine | HCID 57466596 | 42.7% |
Reaction Steps
A solution of trimethyl(prop-1-yn-1-yl)silane (1.7 g, 11.48 mmol), 3,5-dibromopyridine (2.72 g, 11.48 mmol), Pd(PPh3)4 (0.66 g, 0.57 mmol), TBAF (1.0 M solution in THF, 11.48 mL, 11.48 mmol), copper(I) iodide (0.66 g, 3.44 mmol), and triethylamine (5.28 mL, 37.9 mmol) was stirred at rt for 12 h. The reaction mixture was worked up with EtOAc and water, and the crude product was purified by silica gel chromatography eluting with 0-3% EtOAc/Hexanes to give the title compound as a white solid (0.96 g, 42% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 8.55 (dd, J=12.3, 2.0 Hz, 2H), 7.83 (t, J=1.9 Hz, 1H), 2.10 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08598161B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-18667f7e12984d6ca36605fdac789c2d |
| Source note | uspto-grants-2013_12 |