2-Fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile
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Chemical Product Description & Applications
This fluorobenzonitrile-substituted benzylidene phthalide is an unsaturated lactone intermediate used before formation of the olaparib phthalazinone ring. The exocyclic alkene establishes the connection between two aromatic fragments, while the lactone provides the carbonyl framework for nitrogen-ring construction. The pendant nitrile retains a masked carboxyl functionality for later conversion.
The selected compound belongs to the ring-conversion stage, rather than the final piperazine-coupling stage. Reaction with a suitable nitrogen source transforms the phthalide-derived framework into the benzyl-linked phthalazinone structure. Nitrile hydrolysis can then supply the aromatic acid needed downstream. These distinct transformations separate construction of the fused heterocycle from installation of the terminal amide fragment.
Typical Applications
- Phthalazinone-ring synthesis: Used in hydrazine-mediated conversion of the benzylidene lactone into a phthalazinone intermediate, preserving the fluorinated benzonitrile substituent.
- Olaparib aromatic-acid precursor production: Used upstream of the acid fragment in sequences that combine heterocycle formation with subsequent nitrile conversion before piperazine amide assembly.
Specifications
| Parameter | Specification | Test Method |
|---|---|---|
| Appearance | Solid; color consistent with the reference sample | Visual inspection |
| Identification | Consistent with authenticated reference | FTIR fingerprint comparison |
| Chromatographic purity | ≥98.0 area% | HPLC with suitable UV or CAD detection |
| Total organic impurities | ≤2.0 area% | HPLC, area normalization |
| Largest individual impurity | ≤1.0 area% | HPLC, area normalization |
| Water | ≤1.0% w/w | Karl Fischer titration |
Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.
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