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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 556867Generated: October 25, 2026

Sodium Carbonate → (E)-tert-Butyl 4-((2-chloro-5-(3-methoxyprop-1-enyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

https://huagongshe.com/reaction/556867

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 16217443—
ReactantTert-butyl 4-(((2-chloro-5-iodopyridin-4-yl)amino)methyl)piperidine-1-carboxylateHCID 59613389—
CatalystHCID 178418397HCID 178418397—
SolventAcetonitrileHCID 6342—
Product(E)-tert-Butyl 4-((2-chloro-5-(3-methoxyprop-1-enyl)pyridin-4-ylamino)methyl)piperidine-1-carboxylateHCID 5961350365.4%

Reaction Steps

A solution of tert-butyl 4-((2-chloro-5-iodopyridin-4-ylamino)methyl)piperidine-1-carboxylate (Synthesis 170-B) (0.100 g, 0.22 mmol), (E)-2-(3-methoxyprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.044 g, 0.22 mmol), sodium carbonate (0.5 M, 0.66 mL) and tetrakis(triphenylphosphine)palladium(0) (0.013 g, 0.01 mmol) in acetonitrile (2.00 mL) was heated under microwave irradiation for 20 min at 100° C. The solvent was removed in vacuo and the crude product was purified by silica column chromatography, eluting with ethyl acetate and hexane (1/1). to give the title compound as a colourless oil (0.057 g, 65%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058045B2
Source datasetuspto-grants-2011_11
ORD IDord-202edd73fb2c44919841fed0d0998254
Source noteuspto-grants-2011_11