Reaktion #52321

Reaktionsgleichung

3-chloro-propionic acid ethyl ester

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

sodium hydride

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title product

Ausbeute 45.3%

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

Ausbeute 45.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle