반응 #2487470

반응 방정식

methyl 6-chloromethylpyridine-2-carboxylate

ammonium chloride

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

sodium hydride

→

title compound

수율 69.7%

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

수율 69.7%

용매

water

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   온도cooling
3. 3
   workup.STIRRINGby stirring at 80° C. for 21 hours
4. 4
   추출followed by extraction with ethyl acetate
5. 5
   세척The organic layer was washed with water and saturated brine successively
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

실험 절차

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).

출처