반응 #52322

반응 방정식

3-bromo-hexanoic acid ethyl ester

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

sodium hydride

→

title product

수율 17.0%

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

수율 17.0%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight
2. 2
   기타quenched with water
3. 3
   추출The crude product was extracted with methylene chloride
4. 4
   세척washed with brine
5. 5
   기타purified via column chromatography with silica gel (ethyl acetate/hexane:1:1)

실험 절차

To a solution of 2-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridine (0.18 g, 0.62 mmol) in DMF (2 mL) was added sodium hydride (30.0 mg, 1.24 mmol) at room temperature. After stirring for 15 minutes, 3-bromo-hexanoic acid ethyl ester (276 mg, 1.24 mmol) was added. The reaction mixture was stirred overnight and quenched with water. The crude product was extracted with methylene chloride, washed with brine, and purified via column chromatography with silica gel (ethyl acetate/hexane:1:1), to give the title product (17% yield). 1H NMR (CDCl3) δ 9.08 (dd, J=1.7, 4.0 Hz, 1H), 8.14 (m, 1H), 8.06 (m, 1H), 7.32-7.44 (m, 4H), 7.05-7.12 (m, 2H), 6.45 (d, J=3.2 Hz, 1H), 4.81 (m, 1H), 3.99 (m, 2H), 3.08 (m, 2H), 2.83 (m, 4H), 2.22 (m, 2H), 1.90 (m, 2H), 1.20 (m, 2H), 1.07 (m, 3H), 0.87 (m, 3H). Mass Spectrum (LCMS, ESI) calculated for C27H32N3O2 430.3 (M+H); found 430.3.

출처