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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1405787Generated: October 31, 2026

Sodium Carbonate Decahydrate → 3-(6-Methoxynaphthalen-2-yl)pyridin-2-amine

https://huagongshe.com/reaction/1405787

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium Carbonate DecahydrateHCID 151402—
Reactant2-Amino-3-bromopyridineHCID 817700—
Reactant6-Methoxy-2-naphthaleneboronic acidHCID 4641692—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
Product3-(6-Methoxynaphthalen-2-yl)pyridin-2-amineHCID 65550144115.6%

Reaction Conditions

Temperature70 °C

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (95 mg) was added to a suspension of 3-bromopyridin-2-amine (713.7 mg), 6-methoxynaphthalen-2-ylboronic acid (1000 mg) and sodium carbonate decahydrate (2361 mg) in DME (15 mL) and water (3 mL) and the mixture was stirred at 80° C. under nitrogen for 3 hr and at 70° C. overnight. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc) and the volatiles were removed in vacuo to give the title compound (1194 mg) as a crude orange solid. This product was subjected to the next reaction without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08916551B2
Source datasetuspto-grants-2014_12
ORD IDord-34394939926c4b019ae2340cca11ad75
Source noteuspto-grants-2014_12