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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1666551Generated: November 4, 2026

Dimethylformamide → Tert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylate

https://huagongshe.com/reaction/1666551

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantCesium carbonateHCID 10796—
Reactant1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 4184869—
ReactantHCID 178516739HCID 178516739—
SolventWaterHCID 962—
ProductTert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylateHCID 5845666996.7%

Reaction Conditions

Temperature90 °C

Reaction Steps

Cesium carbonate (372 mg) was added to a DMF solution (2 ml) of 2-bromo-5-hydroxypyrazine (100 mg) and 1-t-butoxycarbonyl-4-(methanesulfonyloxy)piperidine (192 mg), and stirred at 90° C. for 14 hours. The reaction mixture was cooled to room temperature, water was added thereto and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane:ethyl acetate=1:11) to obtain the entitled compound (198 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08044070B2
Source datasetuspto-grants-2011_10
ORD IDord-33d126b29dd34a709777559deb4793ff
Source noteuspto-grants-2011_10