HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Phenoxybenzaldehyde → HCID 9890534, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Phenoxybenzaldehyde | HCID 66139 | — |
| Reactant | (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 15548053 | — |
| Reactant | HCID 18359319 | HCID 18359319 | — |
| 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 | HCID 9890534 | HCID 9890534 | — |
Reaction Steps
Using Method C above, 3-hydroxy-3-(4-phenoxyphenyl)-1-propyne (200 mg, 0.89 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 4-phenoxybenzaldehyde (Aldrich) according to Method A above) was coupled to (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 2) (146 mg, 0.40 mmol) using (Ph3P)2PdCl2 (30 mg) (Aldrich) and CuI (16 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-phenoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 100 mg, 54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-88b12d35e75b49efbef6f69866458d4e |
| Source note | uspto-grants-2001_11 |