Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Heptane | HCID 8900 | — |
| Reactant | HCID 10867408 | HCID 10867408 | — |
| Reactant | 4-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one | HCID 118131255 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118150078 | HCID 118150078 | 91.5% |
Reaction Steps
To a solution of 4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 2.65 g, 9.84 mmol) in dry DMF (30 ml), benzyl methyl(prop-2-yn-1-yl)carbamate (Intermediate G22, 4 g, 19.68 mmol), copper(I) iodide (0.562 g, 2.95 mmol), tetrakis(triphenylphosphine)palladium(0) (1.946 ml, 1.476 mmol), benzyl methyl(prop-2-yn-1-yl)carbamate (4 g, 19.68 mmol) and triethylamine (4.04 ml, 29.5 mmol) were added. The resulting suspension was heated to 95° C. overnight. Then, solvent was removed under reduced pressure. The product was purified by Biotage Si 10 g with a gradient of heptane and EtOAc affording the title compound (3.524 g, 9.00 mmol, 91% yield) a yellowish oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09321776B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-f5087b2c534045f7a034870853cbc078 |
|---|
| Source note | uspto-grants-2016_04 |
|---|
