Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | HCID 22724547 | HCID 22724547 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | HCID 5278407 | HCID 5278407 | 66% |
Reaction Steps
To a solution of N-(4-chlorobenzyl)-8-iodo-1-methyl-4-oxo-6-(tetrahydro-2H-pyran-4-ylmethyl)-1,4-dihydro-3-quinolinecarboxamide (0.200 g), PdCl2(PPh3)2 (0.012 g) and CuI (0.029 g) in 10 mL Et2NH and 5 mL CH2Cl2 is added propargyl alcohol (0.021 g). The mixture is allowed to stir overnight at room temperature. The solvents are evaporated and the residue is partitioned between CH2Cl2 and water. The aqueous layer is extracted with CH2Cl2 (3×). The combined organic layers are washed with brine, dried and condensed. The crude product is chromatographed (Biotage flash 40S, eluent 1% MeOH/CH2Cl2 then 2% MeOH/CH2Cl2). Fractions homogeneous by TLC are combined and concentrated. The resulting solid is recrystallized from CH2Cl2/Et20 to yield 0.114 g (66%) of the desired product as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06544990B2 |
|---|
| Source dataset | uspto-grants-2003_04 |
|---|
| ORD ID | ord-acf41478a54442158624b84c1aa041b4 |
|---|
| Source note | uspto-grants-2003_04 |
|---|
