HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl alcohol → (Tert-butoxy)-n-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | [(3-Bromo-4-fluorophenyl)methyl]-carbamic acid tert-butyl ester | HCID 21961437 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | (Tert-butoxy)-n-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide | HCID 131725909 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of tert-butoxy-N-[(3-bromo-4-fluorophenyl)methyl]carboxamide (0.6 g, 2.0 mmol, Step A), CuI (38 mg, 0.2 mmol), PdCl2(PPh3)2 (72 mg, 0.1 mmol), propargyl alcohol (0.35 mL, 6.0 mmol) and TEA (12 mL) was heated at 100° C. for 5 h. The resulting mixture was filtered, and the filtrate was concentrated. The residue was purified by SiO2 chromatography to give the title compound. MS (ES+): 297 (M+NH4)+. Calc'd C15H22FN2O3-297.34.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07101868B2 |
| Source dataset | uspto-grants-2006_09 |
| ORD ID | ord-467be4e71881463fa5aad2e5640c0d28 |
| Source note | uspto-grants-2006_09 |