HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Benzoic acid, 4-amino-2-chloro-5-iodo-, methyl ester | HCID 11839203 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate | HCID 59625799 | — |
Reaction Steps
To a mixture of compound 70n (0.642 mmol, 200 mg), CuI (0.064 mmol, 12.2 mg) and Pd(PPh3)2Cl2 (0.064 mmol, 45 mg) in THF (2 mL) was added ethynyltrimethylsilane (0.963 mmol, 95 mg) followed by Et3N (7.19 mmol, 1 mL) under N2. The reaction mixture was stirred at room temperature for 1.5 h and then partitioned between EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 70p.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08741887B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-8ed563de0d5a4da887a8a382cb1f8ec7 |
| Source note | uspto-grants-2014_06 |