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In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;
General procedure: [00194] This compound was prepared according to the procedure described in the Journal of Medicinal Chemistry 2014, 57(17), 7293 - 7316. Trifluoroacetic anhydride (38 mL, 56.0 g, 0.27 mol) was added dropwise to a solution of 5-fluoro-lH-indole (30.0 g, 0.22 mol) in DMF (300 mL) over 0.5 h at 0C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with water (1 L), after which solids began to form, the mixture was stirred for 0.5 h, then filtered. The solid was collected, washed with water (200 mL><3), then added to aqueous sodium hydroxide (20%, 150 mL, 0.75 mol) and heated under reflux for 8 h. The reaction mixture was cooled and acidified with aqueous 3N HC1 to pH of 3 whereupon a precipitate was produced. The solid was collected by filtration, washed with water (200 mLx3), dried to afford compound 2 (27.1 g, 68% yield) as off-white solid
75%
General procedure: This compound was prepared according to the procedure described in the Journal of Medicinal Chemistry 2014, 57(17), 7293- 7316. Trifluoroacetic anhydride (38 mL, 56.0 g, 0.27 mol) was added dropwise to a solution of 5-fluoro-1H-indole (30.0 g, 0.22 mol) in DMF (300 mL) over 0.5 h at 0C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with water (1 L), after which solids began to form, the mixture was stirred for 0.5 h, then filtered. The solid was collected, washed with water (200 mL×3), then added to aqueous sodium hydroxide (20%, 150 mL, 0.75 mol) and heated under reflux for 8 h. The reaction mixture was cooled and acidified with aqueous 3N HCl to pH of 3 whereupon a precipitate was produced. The solid was collected by filtration, washed with water (200 mL×3), dried to afford compound 2 (27.1 g, 68% yield) as off-white solid.
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[ 858515-66-9 ]
7-fluoro-1-methyl-N-(quinolin-8-yl)-1H-indole-3-carboxamide[ No CAS ]
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