反应 #2487470

反应方程式

methyl 6-chloromethylpyridine-2-carboxylate

ammonium chloride

2-(butan-2-yl)-6-chloro-5-methoxy-1H-indole

sodium hydride

→

title compound

收率 69.7%

Methyl 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylate

收率 69.7%

溶剂

water

N,N-dimethylformamide

反应条件

后处理

1. 1
   温度cooling
2. 2
   温度cooling
3. 3
   workup.STIRRINGby stirring at 80° C. for 21 hours
4. 4
   萃取followed by extraction with ethyl acetate
5. 5
   洗涤The organic layer was washed with water and saturated brine successively
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

To a solution of 2-(butan-2-yl)-6-chloro-5-methoxy-1H-indole (289 mg) in N,N-dimethylformamide (6.1 mL) was added sodium hydride (dispersed in liquid paraffin, 55% or more, 73 mg) under ice-cooling. This mixture was stirred for 1 hour under ice-cooling. Subsequently, methyl 6-chloromethylpyridine-2-carboxylate (271 mg) was added thereto, followed by stirring at 80° C. for 21 hours. The reaction mixture was cooled to room temperature, and then saturated aqueous ammonium chloride solution/water (2/1, 30 mL) was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (328 mg). 1H-NMR (CDCl3) δ ppm: 0.84 (3H, t, J=7.4 Hz), 1.23 (3H, d, J=6.9 Hz), 1.45-1.80 (2H, m), 2.60-2.75 (1H, m), 3.93 (3H, s), 4.06 (3H, s), 5.50 (2H, s), 6.31 (1H, s), 6.40-6.50 (1H, m), 7.12 (1H, s), 7.15 (1H, s), 7.64 (1H, t, J=7.9 Hz), 7.95-8.05 (1H, m).

来源