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ChemicalBook CAS DataBase List 6-BROMO-4-FLUORO-1H-INDAZOLE
885520-23-0

6-BROMO-4-FLUORO-1H-INDAZOLE synthesis

5synthesis methods
4-Bromo-2,6-difluorobenzaldehyde

537013-51-7

6-BROMO-4-FLUORO-1H-INDAZOLE

885520-23-0

4-Bromo-2,6-difluorobenzaldehyde (CAS 537013-51-7, 442.0 mg, 2.00 mmol) was suspended in ethylene glycol (10 mL) at room temperature, and hydrazine monohydrate (0.19 mL, 4.00 mmol) was slowly added with stirring. The reaction mixture was heated to 95 °C under nitrogen protection and maintained at this temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to 5 °C and diluted with deionized water. Subsequently, the reaction solution was extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 6-bromo-4-fluoro-1H-indazole (430.0 mg, 100% yield) as a yellow solid.

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Yield: 100%

Reaction Conditions:

with hydrazine hydrate in ethylene glycol at 95; for 2 h;Inert atmosphere;

Steps:

5.1.13. 6-Bromo-4-fluoro-1H-indazole (21)
To a stirred suspension of 4-bromo-2,6-difluorobenzaldehyde 20 (commercially available, CAS 537013-51-7, 442.0 mg, 2.00 mmol) in ethylene glycol (10 mL) at ambient temperature was added hydrazine monohydrate (0.19 mL, 4.00 mmol). The resulting suspension was heated to 95 C under nitrogen for 2 h.The reaction was then cooled to 5 C and diluted with water. The solution was extracted with ethyl acetate, dried over anhydrous Na2SO4, and concentrated to yield 6-bromo-4-fluoro-1H-indazole 21 (430.0 mg, 100%) as a yellow solid.

References:

Qian, Shan;He, Tao;Wang, Wei;He, Yanying;Zhang, Man;Yang, Lingling;Li, Guobo;Wang, Zhouyu [Bioorganic and Medicinal Chemistry,2016,vol. 24,# 23,p. 6194 - 6205]

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