Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylarsine | HCID 11773 | — |
| Reactant | 2-(Tri-n-butylstannyl)thiophene | HCID 2779373 | — |
| Reactant | HCID 178418840 | HCID 178418840 | — |
| Reactant | HCID 178484165 | HCID 178484165 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178484164 | HCID 178484164 | — |
Reaction Steps
A mixture of 40 mg of Example 9 (4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-9-[(1,2-oxazinan-2-ylacetyl)amino]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, 6 mg Pd(PPh3)2Cl2 (dichlorobis(triphenyl-phosphine)palladium(II), 2 mg AsPh3, 2 mg Cul (copper(1) iodide) and 2-(tributylstannyl)-thiophene in 10 mL toluene is heated to reflux under nitrogen for ca. 6 h. The reaction mixture is cooled, filtered and solvent removed. The crude residue is dissolved in water at pH 2 (by adding 10% HCl), and 10% ammonium hydroxide is added to adjust the pH to about 4 followed by extraction with methylene chloride. Organic layer dried over sodium sulfate, solvent removed and residue triturated with ether and 1M HCl in ether to give 8 mg of the product of the example.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07812008B2 |
|---|
| Source dataset | uspto-grants-2010_10 |
|---|
| ORD ID | ord-73f3603056564e57aa3bca917b9ebedc |
|---|
| Source note | uspto-grants-2010_10 |
|---|
