HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Hydroxybenzaldehyde → HCID 10156965, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Hydroxybenzaldehyde | HCID 101 | — |
| Reactant | (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 18359254 | — |
| Reactant | HCID 18359312 | HCID 18359312 | — |
| 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 10156965 | HCID 10156965 | — |
Reaction Steps
Using Method D above, 3-hydroxy-3-(3-hydroxyphenyl)-1-propyne (140 mg, 0.94 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 3-hydroxybenzaldehyde (Aldrich) through 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) (200 mg, 0.63 mmol) using (Ph3P)2PdCl2 (68 mg) (Aldrich) and CuI (32 mg) (Aldrich) as catalyst in DMF (4 mL) and Et3N (4 mL) as solvent at 80° C. for 15 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(3-hydroxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 82 mg, 31%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-897fa9c0dfa94ad8ae5151bf541fae96 |
| Source note | uspto-grants-2001_11 |