Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Bromo-2-chloropyridine | HCID 3847770 | — |
| Reactant | 2-(4-Fluorophenyl)pyrrolidine | HCID 3865560 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 86673615 | HCID 86673615 | 57.8% |
Reaction Steps
4-Bromo-2-chloro-pyridine (0.17 mL, 1.5 mmol), 2-(4-fluoro-phenyl)-pyrrolidine (250 mg, 1.5 mmol) and triethylamine (0.22 mL, 1.6 mmol) are mixed in DMSO (5.0 mL). The reaction mixture is heated at 120° C. for 30 min and 200° C. for 40 min in a microwave reactor. Then water (35 mL) is added and the mixture is extracted with EtOAc (3×30 mL). The organic layers are combined, washed with water (3×20 mL) and concentrated to give the crude product. Purification by silica flash column chromatography using EtOAc in heptane (gradient from 10% to 90%) followed by Gilson preparative HPLC affords 240 mg of desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722709B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-40fd944b24854e6b922bd3f7a25ae573 |
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| Source note | uspto-grants-2014_05 |
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