반응 #659314

반응 방정식

5-methylpyridin-3-ylboronic acid

Na2CO3

2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde

→

title compound

수율 80.0%

7-Fluoro-8-methyl-2-(5-methylpyridin-3-yl)quinoline-3-carbaldehyde

수율 80.0%

용매

water

DME

반응 조건

후처리

1. 1
   기타Prepared
2. 2
   기타The crude material was triturated in diethyl ether (75 mL)
3. 3
   여과the solid was filtered off
4. 4
   기타dried under vacuum

실험 절차

Prepared according to the procedure described for Intermediate 41, utilising 2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde (5.0 g, 22.36 mmol), 5-methylpyridin-3-ylboronic acid (6.95 g, 50.75 mmol), tetrakis(triphenylphosphine)palladium(0) (258 mg, 0.22 mmol) and Na2CO3 (3.55 g, 33.54 mmol) in water (30 mL) and DME (60 mL). The crude material was triturated in diethyl ether (75 mL), and the solid was filtered off and dried under vacuum to give the title compound (5.0 g, 80%) as a brown solid. δH (DMSO-d6) 10.12 (s, 1H), 9.06 (s, 1H), 8.72 (d, J 1.9 Hz, 1H), 8.60 (d, J 1.5 Hz, 1H), 8.24 (dd, J 9.0, 6.4 Hz, 1H), 7.99 (d, J 0.6 Hz, 1H), 7.68 (t, J 9.2 Hz, 1H), 2.66 (d, J 2.4 Hz, 3H), 2.44 (s, 3H). LCMS (ES+) 281 (M+H)+, RT 1.66 minutes.

출처