반응 #52321

반응 방정식

3-chloro-propionic acid ethyl ester

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

sodium hydride

→

title product

수율 45.3%

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

수율 45.3%

용매

DMF

반응 조건

후처리

1. 1
   온도After cooling to 0° C.
2. 2
   workup.STIRRINGstirred overnight at room temperature
3. 3
   추출the resulting mixture was extracted with methylene chloride
4. 4
   세척The combined organic layers were washed with water and brine
5. 5
   건조dried over Na2SO4

실험 절차

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).

출처