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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2361691Generated: October 31, 2026

Sodium hydride → HCID 58243409, compound

https://huagongshe.com/reaction/2361691

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantCesium fluorideHCID 25953—
Reactant5-Bromo-2-(trifluoromethyl)pyridineHCID 2761197—
ReactantHCID 58243416HCID 58243416—
SolventDimethyl SulfoxideHCID 679—
SolventDichloromethaneHCID 6344—
ProductHCID 58243409HCID 5824340945.9%

Reaction Conditions

Temperature85 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08691804B2
Source datasetuspto-grants-2014_04
ORD IDord-a15dda75db004cc6bc001181501dc26d
Source noteuspto-grants-2014_04