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HRID 1748112Erstellt: 24. Oktober 2026

Sodium hydride → 3-{[7-(2,2,2-Trifluoroethoxy)naphthalen-2-yl]oxy}pyridin-2-amine

https://huagongshe.com/de/reaction/1748112

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium hydrideHCID 24758—
EduktAmmonium ChlorideHCID 25517—
EduktEthanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 67942—
Edukt7-[(2-Aminopyridin-3-yl)oxy]naphthalen-2-olHCID 66747765—
LösungsmittelDimethyl SulfoxideHCID 679—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt3-{[7-(2,2,2-Trifluoroethoxy)naphthalen-2-yl]oxy}pyridin-2-amineHCID 6674776816,9%

Reaktionsbedingungen

Temperatur120 °C

Reaktionsschritte

To a mixture of sodium hydride (60%, 116 mg), 7-[(2-aminopyridin-3-yl)oxy]naphthalen-2-ol (477 mg) and dehydrated THF (10 mL) was added a mixture of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (370 mg) and dehydrated THF (5 mL) at room temperature. The reaction mixture was stirred at 70° C. over the weekend, DMSO (10.00 mL) was added and the mixture was stirred at 120° C. for 1 hr. The reaction mixture was added to a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (82 mg) as a pale-yellow viscous product.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09150591B2
Quelldatensatzuspto-grants-2015_10
ORD IDord-c6d83905303e465b951326268d28f031
Quellennotizuspto-grants-2015_10