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HRID 57768Erstellt: 24. Oktober 2026

4-Bromo-2-methylpyridine → 8-(3-methoxyphenyl)-N-(2-methylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

https://huagongshe.com/de/reaction/57768

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt4-Bromo-2-methylpyridineHCID 2762835—
Edukt(R)-(+)-2,2'-Bis(di(3,5-xylyl)phosphino)-1,1'-binaphthylHCID 4189905—
EduktSodium t-butoxideHCID 23676156—
Edukt8-(3-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamineHCID 59199102—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelTolueneHCID 1140—
Produkt8-(3-methoxyphenyl)-N-(2-methylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amineHCID 4455431739%

Reaktionsbedingungen

Temperatur110 °C

Reaktionsschritte

A suspension of 8-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.150 g, 0.625 mmol, 1 equiv), 4-bromo-2-methylpyridine (0.160 g, 0.935 mmol, 1.5 equiv), tris(dibenzylideneacetone)dipalladium (0) (27.5 mg, 0.03 mmol, 0.05 equiv), sodium tert-butoxide (0.90 g, 0.94 mmol, 1.5 equiv), and 2,2′-bis[di(3,5-xylyl)phosphino]-1,1′-binaphthyl (38.9 mg, 0.625 mmol, 0.1 equiv) in toluene (2 mL) was purged with nitrogen for 15 min. The reaction mixture was heated at 110° C. by microwave for 10 min. The reaction mixture was diluted with ethyl acetate (50 mL) and filtered through celite. The filtrate was then washed with brine (3×20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative HPLC afforded 8-(3-methoxyphenyl)-N-(2-methylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (80 mg, 39%). LCMS (ESI) m/z: 332.1; 1H NMR (400 MHz, DMSO-d6) δ: 10.45 (br s, 1H), 8.81 (dd, J=6.4, 0.8 Hz, 1H), 8.23 (d, J=6.0 Hz, 1H), 7.88 (dd, J=6.8, 0.8 Hz, 1H), 7.74 (s, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.57 (s, 1H), 7.54 (dd, J=6.0, 2.0 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.15 (t, J=6.8 Hz, 1H), 7.00 (dd, J=8.0, 2.4 Hz, 1H), 3.83 (s, 3H), 2.42 (s, 3H).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09434732B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-b476c94d77f24336978f0fd1e5a28383
Quellennotizuspto-grants-2016_09