反応 #52322

反応方程式

3-bromo-hexanoic acid ethyl ester

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

sodium hydride

→

title product

収率 17.0%

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

収率 17.0%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight
2. 2
   その他quenched with water
3. 3
   抽出The crude product was extracted with methylene chloride
4. 4
   洗浄washed with brine
5. 5
   その他purified via column chromatography with silica gel (ethyl acetate/hexane:1:1)

実験手順

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.

出典