Reaktion #427466

Reaktionsgleichung

sodium bicarbonate

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

lithium triethylborohydride

HCl

→

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto quench
2. 2
   Sonstigethe reaction
3. 3
   Temperaturthe mixture was heated
4. 4
   Temperaturto reflux for 30 minutes
5. 5
   SonstigeThe two phases were separated
6. 6
   Extraktionthe aqueous layer was extracted with ethyl acetate (EA)
7. 7
   WaschenThe combined organic layers were washed with brine
8. 8
   Trocknendried over anhydrous MgSO4
9. 9
   Einengenconcentrated en vacuo
10. 10
    SonstigeThe crude material was purified by RP-HPLC
11. 11
    Extraktionfollowed by extraction in DCM

Vorschrift

To a solution of ethyl 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)benzoate (Example 70) (1.0 eq.) in THF (0.1 M) at 0° C. was added 1.0 M lithium triethylborohydride in THF (10 eq.) and warmed to room temperature over 2 hours. 1N HCl aqueous solution was added slowly to quench the reaction, and the mixture was heated to reflux for 30 minutes. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution. The two phases were separated, and the aqueous layer was extracted with ethyl acetate (EA). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by RP-HPLC using a 10-50% MeCN in water gradient followed by extraction in DCM to give (4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenyl)methanol. 1H NMR (Acetone-d6): δ 8.77 (s, 1H), 8.69 (s, 1H), 8.26 (d, 1H), 7.40 (s, 1H), 7.21-7.28 (m, 4H), 7.13 (d, 1H), 6.5 (br, 2H), 4.56 (s, 2H), 4.1 (br t, 1H), 3.10-3.23 (m, 4H), 2.44 (s, 3H). LRMS [M+H]=344.2

Quelle