HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → 2-Bromo-5-trimethylsilanylethynyl-pyrazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 2-Bromo-5-iodopyrazine | HCID 21931200 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | triethylamine N,N-dimethylformamide | HCID 22056947 | — |
| Product | 2-Bromo-5-trimethylsilanylethynyl-pyrazine | HCID 57497686 | — |
Reaction Steps
Reaction of a mixture of 2-bromo-5-iodo-pyrazine and copper (I) iodide under inert conditions in an appropriate solvent and base e.g. DMF/Et3N with ethynyl-trimethyl-silane using a palladium catalyst e.g. Pd(PPh3)4 at room temperature gives 2-Bromo-5-trimethylsilanylethynyl-pyrazine. This material can be used without further purification and reacted to form 6-bromo-2-trimethylsilanyl-pyrazolo[1,5-a]pyrazine using O-(mesitylenesulfonyl)hydroxylamine to form the N-amino adduct. This can then be cyclised by reacting with base e.g. K2CO3 to form pyrazolopyrazine core (Scheme 6).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08859582B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-81e049e814a74a0db2ef93d75d1cf94d |
| Source note | uspto-grants-2014_10 |