Reaktion #427531

Reaktionsgleichung

methallyl bromide

4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenol

potassium carbonate

→

8-methyl-2-(4-(2-methylallyloxy)phenethyl)benzo[f][1,7]naphthyridin-5-amine

Lösungsmittel

ethyl acetate

water

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to ambient temperature
2. 2
   SonstigeThe biphasic layers were separated
3. 3
   Waschenthe aqueous layer was washed twice with ethyl acetate
4. 4
   TrocknenThe combined organic layers were dried over anhydrous Na2SO4
5. 5
   Sonstigethe volatiles were removed in vacuo
6. 6
   SonstigeThe resulting residue was purified by a COMBIFLASH® system (ISCO)

Vorschrift

To a solution of 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenol (from Example 170) (1.0 equiv.) in dimethylformamide (0.10 M) was added anhydrous potassium carbonate (1.5 equiv.) followed by methallyl bromide (1.2 equiv.). The resulting mixture was allowed to stir for 18 hours at 100° C. After cooling to ambient temperature, the mixture was diluted with ethyl acetate and water. The biphasic layers were separated and the aqueous layer was washed twice with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH® system (ISCO) using 0-60% ethyl acetate in hexanes to provide 8-methyl-2-(4-(2-methylallyloxy)phenethyl)benzo[f][1,7]naphthyridin-5-amine as a solid. 1H NMR (Acetone-d6): δ 8.75 (s, 1H), 8.68 (s, 1H), 8.27 (d, 1H), 7.41 (s, 1H), 7.12-7.19 (m, 3H), 6.87 (d, 2H), 6.60 (br, 2H), 5.06 (s, 1H), 4.93 (s, 1H), 4.43 (s, 2H), 3.20 (t, 2H), 3.05 (t, 2H), 2.45 (s, 3H), 1.79 (s, 3H). LRMS [M+H]=384.2

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