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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1405668Generated: October 26, 2026

Sodium Carbonate → 3-[4-(1-Methylpropyl)phenyl]pyridin-2-amine

https://huagongshe.com/reaction/1405668

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Amino-3-bromopyridineHCID 817700—
Reactant4-sec-Butylphenylboronic acidHCID 3690874—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
Product3-[4-(1-Methylpropyl)phenyl]pyridin-2-amineHCID 6555136289.2%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of sodium carbonate (412 mg), tetrakis(triphenylphosphine)palladium(0) (112 mg), 4-(1-methylpropyl)phenylboronic acid (450 mg) and 3-bromopyridin-2-amine (336 mg) in 1,2-dimethoxyethane (15 mL) and water (3 mL) was stirred under a nitrogen atmosphere at 80° C. overnight. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (392 mg) as a pale-yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08916551B2
Source datasetuspto-grants-2014_12
ORD IDord-766d0fd291b147caafae8ac80548a3c6
Source noteuspto-grants-2014_12