HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Bromopyridinium chloride → (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-[(4-pyridinyl)ethynyl]-2H-indol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Bromopyridinium chloride | HCID 88100 | — |
| Reactant | (Z)-1,3-dihydro-4-ethynyl-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 59970997 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-[(4-pyridinyl)ethynyl]-2H-indol-2-one | HCID 10154379 | — |
Reaction Steps
Using Method J above, 4-bromopyridine hydrochloride (110 mg, 0.57 mmol) (Aldrich) was coupled with (Z)-1,3-dihydro-4-ethynyl-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 5) (100 mg, 0.38 mmol) using DPPFPdCl2 (15.4 mg) (Aldrich) and CuI (4 mg) (Aldrich) as catalyst in DMF (5 mL) and Et3N (5 mL) as solvent and heating at reflux for 1 day, yielding (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-[(4-pyridinyl)ethynyl]-2H-indol-2-one. (Yield 70 mg, 54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-71d38809836845e4b2468d1d87a4e51d |
| Source note | uspto-grants-2001_11 |