Tetrahydrofuran → methyl 3-[3-amino-4-(indan-2-yloxy)-5-(1-methyl-1H-indazol-5-yl)phenyl]propionate

Participants

Reaction Steps

To methyl 3-[4-(indan-2-yloxy)-3-(1-methyl-1H-indazol-5-yl)-5-nitrophenyl]propionate (13.0 g), THF (138 ml), stabilized nickel (4.42 g, NIKKI CHEMICAL) and water (4 ml) were added, the mixture was stirred, then the interior of the system was purged with hydrogen, and the reaction was allowed under a hydrogen atmosphere at 50° C. for 7 hours with stirring. After confirming the completion of the reaction, the reaction solution was purged with nitrogen and filtered to obtain a filtrate, and the residue on the filter was washed with THF (34 ml) to obtain a wash solution. The filtrate and the wash solution were combined, activated carbon (2.6 g, Japan Envirochemical) was added to the combined solution, and the mixture was stirred for 1 hour at room temperature. The suspension was filtered to obtain a filtrate, and the residue on the filter was washed with THF (34 ml) to obtain a wash solution. Then, the resulting filtrate and the wash solution were combined, water (207 ml) was added to the combined solution over 1 hour, and the mixture was stirred for another 1 hour under ice cooling. Then, this mixture was filtered, and the solid on the filter was washed with water (68 ml) to obtain wet solid. This wet solid was dried under reduced pressure at 50° C. to obtain crystals of methyl 3-[3-amino-4-(indan-2-yloxy)-5-(1-methyl-1H-indazol-5-yl)phenyl]propionate (10.3 g).

Provenance & Evidence