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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 384707Generated: October 27, 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/384707

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—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
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 numberUS08367658B2
Source datasetuspto-grants-2013_02
ORD IDord-73cc97151a5f44d9ade00c7204310011
Source noteuspto-grants-2013_02