Reaktion #2182475

Reaktionsgleichung

mixture

1-(4-methoxybenzyl)-3-(3-(naphthalen-1-yloxy)propyl)-7-o-tolyl-1H-indole-2-carbonitrile

NaN3

NH4Cl

→

7-(2-methylphenyl)-3-(3-(1-naphthyloxy)propyl)-2-(1H-tetraazol-5-yl)-1H-indole

Lösungsmittel

N, N-dimethylamide

dichloromethane trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux overnight
2. 2
   EinengenThe mixture was concentrated under vacuum
3. 3
   Sonstigethe residue was partitioned between ethyl acetate (200 ml) and water (60 ml)
4. 4
   WaschenThe organic phase was washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   SonstigeConcentration of the solvent gave crude product which
7. 7
   EinengenThe mixture was concentrated
8. 8
   workup.DISSOLUTIONthe residue was dissolved in dimethylsulfoxide/methanol (1/1, 2 ml)
9. 9
   Sonstigeloaded on HPLC for purification

Vorschrift

To a mixture of EXAMPLE 581D (232 mg) in N, N-dimethylamide (10 ml) was added NaN3 (281 mg) and NH4Cl (231 mg). The mixture was stirred at reflux overnight. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (200 ml) and water (60 ml). The organic phase was washed with brine and dried over Na2SO4. Concentration of the solvent gave crude product which was dissolved in dichloromethane/trifluoroacetic acid (1:1, 4 ml) and heated to 125° C. in a microwave (CEM Discover) for 20 minutes. The mixture was concentrated and the residue was dissolved in dimethylsulfoxide/methanol (1/1, 2 ml) and loaded on HPLC for purification. 1H NMR (300 MHz, DMSO-d6) δ 10.63 (m, 1H), 8.26 (m, 1H), 7.86 (m, 1H), 7.74 (d, 1H), 7.53 (m, 2H), 7.42 (m, 5H), 7.33 (m, 2H), 7.11 (m, 3H), 6.90 (d, 1H), 4.23 (t, 2H), 2.29 (m, 2H), 2.13 (s, 3H).

Quelle