HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Triisopropylsilylpyrrole → 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Triisopropylsilylpyrrole | HCID 145136 | — |
| Reactant | 1-Bromo-3-ethynylbenzene | HCID 11480818 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole | HCID 68700899 | 670.9% |
Reaction Steps
A solution of N-triisopropylsilylpyrrole (3.49 g, 1 mmol), 3-bromo-1-ethynylbenzene (1.81 g, 1 mmol), Pd(PPh3)4 (800 mg) and CuI (185 mg) in CH3CN (15 ml) and triethylamine (35 ml) is refluxed for 5 h. The reaction mixture is cooled to room temperature and the solvent is evaporated on a rotary evaporator. The crude material is purified by flash chromatographied (silica gel, 100% hexane) to afford 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole (2.7 g, 85%) as a clear oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07705030B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-da4faf1842ba4d4388469f2d95d08be5 |
| Source note | uspto-grants-2010_04 |