HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Ethynylbenzoic acid methyl ester → Methyl 3-((4-(2-acetamidopropyl)phenyl)ethynyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Ethynylbenzoic acid methyl ester | HCID 11275159 | — |
| Reactant | N-(1-(4-Iodophenyl)propan-2-YL)acetamide | HCID 66611344 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 3-((4-(2-acetamidopropyl)phenyl)ethynyl)benzoate | HCID 66611163 | — |
Reaction Steps
To 10.0 g (63.4 mmol) methyl 3-ethynylbenzoate (J. Org. Chem. 1981, 46, 2280-6) and 7.00 g (23.1 mmol) N-(1-(4-iodo-phenyl)propan-2-yl)acetamide (I52.1) in 80 mL DMF are added 100 mL TEA, 250 mg (1.31 mmol) CuI and 1.20 g (1.71 mmol) bis(triphenylphosphine)-palladium (II) chloride. After stirring over night r.t. the solvents are removed under reduced pressure. The residue is partitioned between EtOAc and diluted aq. NH4Cl solution. The organic layer is separated and the aq. layer is extracted with EtOAc (2×). The org. layers are combined, washed with brine, dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, EtOAc 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08835472B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-80a171854e3a4cd182eb4751a6186526 |
| Source note | uspto-grants-2014_09 |