Ammonium Chloride → 3-cyclopropyl-1-((5-methyl-1,3,4-thiadiazol-2-yl)methyl)-1H-indazol-4-amine

Participants

Reaction Steps

To a suspension of 2-((3-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-5-methyl-1,3,4-thiadiazole (61.7 mg, 0.196 mmol) in 4:1 EtOH/H2O (2 mL) was added iron powder (0.219 g, 3.91 mmol) and ammonium chloride (10.5 mg, 0.196 mmol). The reaction mixture was heated to reflux for three hours. The reaction mixture was cooled to ambient temperature, diluted with excess dichloromethane, and the resulting suspension was dried over anhydrous sodium sulfate. The solids were removed by filtration, and the filtrate was concentrated under reduced pressure. The crude product was dissolved in dichloromethane, passed through a silica plug, eluting with 10% MeOH/DCM, and concentrated under reduced pressure to afford the product (27 mg) as a yellow solid.

Provenance & Evidence