HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Thiophenecarboxaldehyde → HCID 9885990, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Thiophenecarboxaldehyde | HCID 68135 | — |
| Reactant | HCID 11205786 | HCID 11205786 | — |
| Reactant | (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 18359254 | — |
| 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 9885990 | HCID 9885990 | — |
Reaction Steps
Using Method D above, 3-hydroxy-3-(thiophen-3-yl)-1-propyne (131 mg, 0.95 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 3-thiophenecarboxaldehyde (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 (107 mg, 0.34 mmol) (Starting Material 1) using (Ph3P)2PdCl2 (32 mg) (Aldrich) and CuI (17 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. or 18 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(thiophen-3-yl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 93 mg, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-f2db1fa430754f1f9233cb161ef77410 |
| Source note | uspto-grants-2001_11 |