Hydrazine → 3-(4-isopropylpyrimidin-2-yl)-1H-indole-5-carbohydrazide

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Reaction Conditions

Reaction Steps

A light-yellow mixture of methyl 3-(4-isopropylpyrimidin-2-yl)-1-tosyl-1H-indole-5-carboxylate (1.37 g, 3.05 mmol) in anhydrous hydrazine (2.39 mL, 76 mmol) and dioxane (1 mL) was heated in an oil bath at 90° C. for 3 h. The mixture was cooled to RT, treated with 20 mL of ice cold H2O. The precipitated pink solid was filtered, rinsed with 2×5 mL of water and 2×20 mL of EtOAc. The filtrate was transferred to a separatory funnel. The aqueous layer was discarded. The EtOAc layer was concentrated to half of its volume. The precipitated brown solid was filtered, rinsed with 2×2 mL of Et2O. The above obtained pink solid and brown solid were combined and dried in a vacuum oven at 40° C. for 18 h to afford 3-(4-isopropylpyrimidin-2-yl)-1H-indole-5-carbohydrazide (400 mg). This material was used in next step without further purification. MS (ESI, pos. ion) m/z: 296.1 (M+1).

Provenance & Evidence