反応 #1608836

反応方程式

sodium carbonate

7-bromo-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-6-carbonitrile

(5-fluoropyridin-3-yl)boronic acid

1,4-dioxan

→

title compound

7-(5-fluoropyridin-3-yl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-6-carbonitrile

溶媒

water

反応条件

後処理

1. 1
   その他Reaction mass
2. 2
   その他was purged with argon for 20 min
3. 3
   ろ過The reaction mixture was filtered through celite bed
4. 4
   ろ過filter bed
5. 5
   洗浄was thoroughly washed with ethyl acetate
6. 6
   濃縮The collected organic part was concentrated under vacuum
7. 7
   その他to afford the crude compound, which
8. 8
   その他was purified by silica gel column chromatography

実験手順

To a stirred solution of 7-bromo-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-6-carbonitrile (145-4; 0.20 g, 0.0006 mol) and (5-fluoropyridin-3-yl)boronic acid (0.97 g, 0.0006 mol) in the mixture of 1,4-dioxan (10 mL) and water (10 mL) was added sodium carbonate (0.190 g, 0.0018). Reaction mass was purged with argon for 20 min. Then catalyst Pd(dppf)2Cl2 (0.048 g, 0.00006 mol) was added and allowed to stir at 80° C. for 12 h. The reaction mixture was filtered through celite bed and filter bed was thoroughly washed with ethyl acetate. The collected organic part was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.739-8.732 (d, J=2.8 Hz, 1H), 8.685 (s, 1H), 8.095-8.066 (d, J=11.6 Hz, 2H), 7.782-7.742 (d, J 8 Hz, 1H), 3.282-3.240 (t, J=8.8 Hz, 2H), 3.143-3.109 (t, J=7.6 Hz, 2H), 2.702 (s, 3H). MS (M+1): 306.1

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