반응 #85689

반응 방정식

2-bromothiazole-5-carbaldehyde

(6-methylpyridin-3-yl)boronic acid

dichloromethane

sodium carbonate

→

2-(6-methylpyridin-3-yl)thiazole-5-carbaldehyde

수율 41.4%

용매

ethyl acetate

water

1,2-dimethoxyethane

반응 조건

후처리

1. 1
   기타The layers were separated
2. 2
   추출the aqueous layer was extracted with ethyl acetate (2×25 mL)
3. 3
   세척The combined organic extracts were washed with saturated aqueous sodium chloride (30 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

A mixture of 2-bromothiazole-5-carbaldehyde (400 mg, 2.08 mmol), (6-methylpyridin-3-yl)boronic acid (428 mg, 3.12 mmol, 1.5 equiv), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (170 mg, 0.21 mmol, 0.1 equiv) and 2.0 M aqueous sodium carbonate (5.2 mL, 10.4 mmol, 5 equiv) in 1,2-dimethoxyethane (6.9 mL) was heated in a microwave reactor at 110° C. for 20 minutes. The reaction was then diluted with ethyl acetate (50 mL) and water (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (30 mL), dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc) provided 2-(6-methylpyridin-3-yl)thiazole-5-carbaldehyde (0.176 g, brown solid) in 41% yield. 1H NMR (400 MHz, CDCl3) δ 10.08 (s, 1H), 9.15 (d, J=2.0 Hz, 1H), 8.47 (s, 1H), 8.19 (dd, J=8.1, 2.4 Hz, 1H), 7.31 (d, J=8.3 Hz, 1H), 2.66 (s, 3H). MS m/z 205.0 (M+H)+; Rt-0.36 min.

출처