HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methoxybenzaldehyde → HCID 10111588, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methoxybenzaldehyde | HCID 11569 | — |
| Reactant | (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 18359254 | — |
| Reactant | 1-(3-Methoxyphenyl)prop-2-yn-1-ol | HCID 18359308 | — |
| 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 10111588 | HCID 10111588 | — |
Reaction Steps
Using Method D above, 3-hydroxy-3-(3-methoxyphenyl)-1-propyne (151 mg, 1.0 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 3-methoxybenzaldehyde (Aldrich) according to Method A 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) (220 mg, 0.69 mmol) using (Ph3P)2PdCl2 (100 mg) (Aldrich) and CuI (55 mg) (Aldrich) as catalyst in DMF (5 mL) and Et3N (5 mL) as solvent at 70° C. for 18 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 66 mg, 24%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-5e2b5f8ae2db4bf98b4d0d50b8325be3 |
| Source note | uspto-grants-2001_11 |