HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 877107Generated: October 25, 2026
Pyrrolidine → 4-(3-Fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)benzenamine
https://huagongshe.com/reaction/877107
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | (Triisopropylsilyl)acetylene | HCID 2734682 | — |
| Reactant | 2-Bromo-1-(3-fluorobenzyloxy)-4-nitrobenzene | HCID 21874800 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(3-Fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)benzenamine | HCID 67504232 | — |
| Product | (2-(2-(3-Fluorobenzyloxy)-5-nitrophenyl)ethynyl)triisopropylsilane | HCID 67504616 | — |
Reaction Steps
To a solution of 1-((2-bromo-4-nitrophenoxy)methyl)-3-fluorobenzene (1 g), ethynyltriisopropylsilane (1.032 mL), pyrrolidine (0.3 mL) in DMF (20 mL) was added Pd(PPh3)2Cl2 (501 mg), CuI (117 mg) and the mixture was heated at 80° C. overnight. The solvent was removed, the residue was purified by flash chromatography, eluting with 10% EtOAc in hexane to give the desired product (2-(2-(3-fluorobenzyloxy)-5-nitrophenyl)ethynyl)triisopropylsilane (compound 23.1, 472 mg) and 4-(3-fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)benzenamine (compound 23.2, 440 mg). LCMS ESI(+) m/z: 428 (M+1) and LCMS ESI(+) m/z: 398 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08987284B2 |
|---|
| Source dataset | uspto-grants-2015_03 |
|---|
| ORD ID | ord-bb93d7f4e3504348a5942ac9dd67077c |
|---|
| Source note | uspto-grants-2015_03 |
|---|
