Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 5-Bromo-2-(trifluoromethyl)pyridine | HCID 2761197 | — |
| Reactant | HCID 58243416 | HCID 58243416 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58243409 | HCID 58243409 | 45.9% |
Reaction Steps
To a solution of {1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}methano 1 (20 mg, 74 μmol) in DMSO (1 ml) was added NaH (6 mg of a 60% dispersion in mineral oil, 0.15 mmol). After 30 minutes CsF (12 mg, 74 μmol) and 5-bromo-2-trifluoromethylpyridine (34 mg, 0.15 mmol) were added and the mixture was heated at 85° C. for 2 hours. The reaction was cooled to room temperature, diluted with dichloromethane (20 ml), washed with water (20 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by preparative HPLC to give the title compound (14 mg, 45%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691804B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-a15dda75db004cc6bc001181501dc26d |
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| Source note | uspto-grants-2014_04 |
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