HuagongsheHuagongshe Chemistry Print Report · For research reference only
(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one → HCID 9929439, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 18359254 | — |
| Reactant | α-Ethynyl-1-methyl-1H-pyrrole-2-methanol | HCID 18359311 | — |
| 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 9929439 | HCID 9929439 | — |
Reaction Steps
Using Method D above, 3-hydroxy-3-(1-methyl-pyrrol-2-yl)-1-propyne (132 mg, 0.98 mmol) (from Example 27 above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (112 mg, 0.35 mmol) (Starting Material 2) using (Ph3P)2PdCl2 (31 mg)(Aldrich) and CuI (17 mg)(Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 28 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(1-methyl-pyrrol-2-yl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 114 mg, 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-2cdfbc0d39bd41c09a98b1b7dce37ccb |
| Source note | uspto-grants-2001_11 |