反応 #52321

反応方程式

3-chloro-propionic acid ethyl ester

2-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridine

sodium hydride

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title product

収率 45.3%

3-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-propionic acid ethyl ester

収率 45.3%

溶媒

DMF

反応条件

後処理

1. 1
   温度After cooling to 0° C.
2. 2
   workup.STIRRINGstirred overnight at room temperature
3. 3
   抽出the resulting mixture was extracted with methylene chloride
4. 4
   洗浄The combined organic layers were washed with water and brine
5. 5
   乾燥dried over Na2SO4

実験手順

To a solution of 2-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridine (0.180 g, 0.627 mmol) in DMF (2 mL) was added sodium hydride (24.0 mg. 1.00 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 h. After cooling to 0° C., 3-chloro-propionic acid ethyl ester (85.0 mg, 0.63 mmol) was added and stirred overnight at room temperature. Ice water was added and the resulting mixture was extracted with methylene chloride. The combined organic layers were washed with water and brine, and dried over Na2SO4. Chromatography of the crude product on silica gel (methylene chloride/methanol, 95:5) gave the title product (0.11 g, 45% yield). 1H NMR (CDCl3) δ 9.08 (d, 1H), 8.13 (d, 1H), 8.08 (d, 1H), 7.30-7.50 (m, 4H), 7.10 (m, 2M), 6.40 (dd, 1H), 4.40 (t, 2H), 4.10 (m, 2H), 3.10 (t, 2H), 2.80 (m, 4H), 2.25 (m, 2H), 1.20 (q, 3H).

出典