HuagongsheHuagongshe Chemistry Print Report · For research reference only
Vanillin → rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Vanillin | HCID 1183 | — |
| Reactant | (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 18359254 | — |
| Reactant | 3-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propyne | HCID 18359256 | — |
| Reactant | HCID 178462451 | HCID 178462451 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 9801994 | — |
Reaction Steps
Using Method D above, 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propyne (197 mg, 1.1 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to vanillin (Aldrich) according to Method B above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 1) (116 mg, 0.36 mmol) using (Ph3P)2PdCl2 (33 mg) (Aldrich) and CuI (18 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 16 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 31 mg, 21%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-38a094e9c37e433f91a2ba6b1936512e |
| Source note | uspto-grants-2001_11 |