HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-phenylprop-1-ynyl)thiazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzylacetylene | HCID 575753 | — |
| Reactant | methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-iodothiazole-4-carboxylate | HCID 59447651 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-phenylprop-1-ynyl)thiazole-4-carboxylate | HCID 90000452 | — |
Reaction Steps
To a solution of Example 15B (1.69 g) in tetrahydrofuran (30 mL) was added bis(triphenylphosphine)palladium (II) dichloride (88 mg), CuI (4.8 mg), prop-2-ynylbenzene (584 mg) and triethylamine (1.5 mL). The mixture was stirred at room temperature for 3 hours, diluted with diethyl ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography, eluting with 10% ethyl acetate in hexanes, to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08883784B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-b82cbdc066a34ae9954b1152f2cf03d0 |
| Source note | uspto-grants-2014_11 |