HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Fluoro-3-iodobenzene → 2-{4-[3-(3-Fluorophenyl)prop-2-ynylidene]piperidin-1-yl}-4-methoxynicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Fluoro-3-iodobenzene | HCID 70725 | — |
| Reactant | 1-Bromo-3,5-difluorobenzene | HCID 136313 | — |
| Reactant | 1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate | HCID 16211673 | — |
| Reactant | 4-(3-Trimethylsilylprop-2-ynylidene)piperidine | HCID 57574982 | — |
| Reactant | 4-Methoxy-2-(4-(3-(trimethylsilyl)prop-2-ynylidene)piperidin-1-yl)nicotinonitrile | HCID 86627351 | — |
| Product | 2-{4-[3-(3-Fluorophenyl)prop-2-ynylidene]piperidin-1-yl}-4-methoxynicotinonitrile | HCID 25181782 | 20.4% |
Reaction Steps
The title compound was prepared in the same way as the Compound of Example 274 but replacing Compound 274c with Compound 294a and 1-bromo-3,5-difluorobenzene with 3-iodofluorobenzene and adding 1 molar equivalent of tetrabutylammonium fluoride monohydrate to the starting reaction mixture. Purification by automated flash chromatography (Horizon™-Biotage) PE-EtOAc 100:30, then by CHCl3 followed by a final purification by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient afforded a colourless oil. Yield: 20.4%. LCPREP. Colourless oil. Yield: 20.4%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518916B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-5cbfa89bb20942aea473d80e46a459a6 |
| Source note | uspto-grants-2013_08 |