Reaktion #7585

Reaktionsgleichung

hydrochloric acid

potassium carbonate

4-chloromethyl-2-methylthiazole

4-chloro-7-hydroxy-6-methoxycinnoline

→

4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline

Ausbeute 48.0%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(prepared
2. 2
   ExtraktionAfter extraction with ethyl acetate
3. 3
   Waschenthe organic layer was washed with water
4. 4
   Trocknenbrine, dried (MgSO4)
5. 5
   Sonstigethe solvent evaporated
6. 6
   SonstigeThe residue was purified by flash chromatography

Vorschrift

The starting material 4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline was obtained by adding potassium carbonate (786 mg, 5.7 mmol) followed by 4-chloromethyl-2-methylthiazole (308 mg, 2 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (0.4 g, 1.9 mmol), (prepared as described for the starting material in Example 10), in DMF (10 ml). After stirring for 4.5 hours at 60° C. the reaction mixture was diluted with water and acidified to pH4 with 2M hydrochloric acid. After extraction with ethyl acetate, the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/ethyl acetate (2/8) as eluent to give 4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline as a solid (293 mg, 48%).

Quelle