HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → 3-((Trimethylsilyl)ethynyl)imidazo[1,2-b]pyridazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Bromoimidazo(1,2-b)pyridazine | HCID 12872319 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-((Trimethylsilyl)ethynyl)imidazo[1,2-b]pyridazine | HCID 66735569 | 71.1% |
Reaction Steps
A mixture of 3-bromoimidazo[1,2-b]pyridazine (36.78 g, 0.186 mol; prepared according to Stanovnik, B. et al. Synthesis (1981), 12, 987-989), ethynyltrimethylsilane (21.89 g, 0.223 mol), Pd(PPh3)4 (10.73 g, 9.29 mmol), CuI (5.30 g, 0.028 mol), and diisopropylethylamine (32.4 mL, 0.279 mol) in 150 mL of DMF was stirred at ambient temperature, under an atmosphere of N2, for 1 h. The reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (eluted with 0-5% MeOH/DCM) to provide 28.46 g of product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278971B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-3fe15107e03648b289b43499d8a6e092 |
| Source note | uspto-grants-2016_03 |