HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 4-Iodophenylacetate → Methyl(4-{4-[(cyclopropyl-ethyl-amino)methyl]-3-methyl-phenylethynyl}-phenyl)-acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 4-Iodophenylacetate | HCID 10378700 | — |
| Reactant | HCID 22568991 | HCID 22568991 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Methyl(4-{4-[(cyclopropyl-ethyl-amino)methyl]-3-methyl-phenylethynyl}-phenyl)-acetate | HCID 18340273 | 53% |
Reaction Steps
Using General Procedure F; cyclopropyl-ethyl-(4-ethynyl-2-methyl-benzyl)-amine (Intermediate 161, 300.0 mg, 1.41 mmols) and methyl-(4-iodophenyl)-acetate (Reagent B, 388.0 mg, 1.41 mmols) in triethylamine (8 mL) was treated with copper(I)iodide (67.0 mg, 0.35 mmol) and sparged with argon for 15 minutes. Dichlorobis(triphenylphosphine)palladium(II) (246 mg, 0.35 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (5-7% EtOAc-hexanes) afforded 270.0 mg (53%) of the title compound as a pale-yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06359135B1 |
| Source dataset | uspto-grants-2002_03 |
| ORD ID | ord-033454007adf4c4e89223a8dbab061a3 |
| Source note | uspto-grants-2002_03 |