反応 #1583813

反応方程式

5-bromo-2-ethyl-4-(4-fluorophenyl)-1,3-thiazole

2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

caesium carbonate

→

4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]-2-methylpyridine

溶媒

THF

反応条件

後処理

1. 1
   ろ過The reaction mixture is then filtered
2. 2
   洗浄the filter cake is washed with ethyl acetate (3×5 ml)
3. 3
   濃縮the combined filtrate is concentrated under reduced pressure
4. 4
   その他The residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

実験手順

In a microwave reactor, 100 mg (0.35 mmol) of 5-bromo-2-ethyl-4-(4-fluorophenyl)-1,3-thiazole, 100 mg (0.45 mmol) of 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 1 ml of a 1M caesium carbonate solution and 28.7 mg (0.04 mmol) of [1,1′-bis(diphenylphosphino)-ferrocene/palladium(II) dichloride dichloromethane complex] in 2.5 ml of THF are, under argon, heated at 90° C. for 25 min. The reaction mixture is then filtered, the filter cake is washed with ethyl acetate (3×5 ml) and the combined filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 35 mg (24%) of the desired product; 1H-NMR(MeCN-d3) δ: 8.34 (d, 1H), 7.47 (m, 3H), 7.12 (s, 1H), 7.07 (m, 2H), 6.99 (d, 1H), 3.03 (q, 2H), 2.42 (s, 3H), 1.38 (t, 3H).

出典