2-Methoxy-5-(trifluoromethyl)phenylboronic acid → 5-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl-amine
Reaktionsgleichung
Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1B(O)O>>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][C:19]=1[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1Komponenten
Versuchsvorschrift
5-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl-amine was prepared from 5-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-yl-amine (0.5 g, 2.3 mmol), and 2-methoxy-5-trifluoromethylbenzeneboronic acid (0.76 g, 3.4 mmol) in a manner analogous to Example 2c. Product was isolated as a foam (0.63 g, 87%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.79-7.73 (m, 2H), 7.49-7.44 (m, 2H), 7.15 (d, J=8.9 Hz, 1H), 6.85 (t, J=4.2 Hz, 1H), 4.45 (brs, 2H), 3.85 (s, 3H). MS=309 (MH)+. 239b) To a stirred solution of 5-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl-amine (0.076 g, 0.25 mmol) in acetonitrile (5 mL, 100 mmol), was added acetic anhydride (0.015 g, 0.15 mmol), at 0° C. along with pyridine (0.02 mL, 0.2 mmol). The reaction was stirred at RT for one hour. White solid was formed that was taken up in dichloromethane and washed with 1N Hydrochloric acid and brine. Organic layer was dried over sodium sulfate and was purified via chromatography utilizing an ISCO automated purification apparatus (silica gel 40 g 5%→100% ethyl acetate in hexane). Product was isolated as a solid (0.043 g, 84%). MP=260-262° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 7.83-7.77 (m, 2H), 7.72 (d, J=8.6 Hz, 1H), 7.60 (t, J=7.6 Hz, 1H), 7.16 (d, J=8.8 Hz, 1H), 7.06 (d, J=8.8 Hz, 1H), 3.87 (s, 3H), 1.6 (s, 3H). MS=351 (MH)+.
Quellen und Nachweise
- ORD-Eintrag
- ord-14e5f3480bca469682808b76c17efe41
- Quelldatensatz
- uspto-grants-2013_08
- Patentnummer
- US08501936B2
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