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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 556861Generated: November 1, 2026

Sodium Carbonate → HCID 59613349, compound

https://huagongshe.com/reaction/556861

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant(4-Methoxyphenyl)boronic acidHCID 201262—
ReactantTert-butyl 4-((2-amino-5-bromopyridin-4-ylamino)methyl)piperidine-1-carboxylateHCID 59613462—
CatalystHCID 178418397HCID 178418397—
SolventAcetonitrileHCID 6342—
ProductHCID 59613349HCID 59613349149.2%

Reaction Conditions

Temperature150 °C

Reaction Steps

Two capped 0.5 mL microwave reaction vials each containing a solution of tert-butyl 4-((2-amino-5-bromopyridin-4-ylamino)methyl)piperidine-1-carboxylate (30 mg, 0.078 mmol), 4-methoxyphenyl boronic acid (17.8 mg, 1.5 eq.), Pd(PPh3)4 (4.5 mg, 5 mol %), 0.5M aqueous sodium carbonate (0.23 mL, 1.5 eq.) in acetonitrile (0.78 mL) were heated at 150° C. for 20 min by microwave irradiation. After cooling, the contents of the two reaction vials were combined and solvents were removed in vacuo. The crude product was purified by chromatography using a Biotage SNAP silica (10 g) column, eluting with a gradient of methanol/NH3 (99/1) in dichloromethane, to give the title compound as a yellow solid (48 mg, 75%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058045B2
Source datasetuspto-grants-2011_11
ORD IDord-c863ea62bec244b7ab73b83b1e9ed575
Source noteuspto-grants-2011_11