6-BROMO-1H-INDAZOL-3-YLAMINE synthesis
- Product Name:6-BROMO-1H-INDAZOL-3-YLAMINE
- CAS Number:404827-77-6
- Molecular formula:C7H6BrN3
- Molecular Weight:212.05
105942-08-3
404827-77-6
Under nitrogen protection, 4-bromo-2-fluorobenzonitrile (5 g, 25.13 mmol) was dissolved in 20 mL of n-butanol, followed by hydrazine hydrate (1.04 mL, 50.26 mmol). The reaction mixture was heated to reflux and kept for 4 hours. Upon completion of the reaction, it was cooled to room temperature and a large amount of solid was observed to precipitate. The solid product was collected by diafiltration and the filter cake was washed with petroleum ether to remove impurities. Finally, the resulting white solid was dried to give 4.759 g of the target product 6-bromo-1H-indazol-3-amine in 85.7% yield.
105942-08-3
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404827-77-6
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Yield:404827-77-6 94%
Reaction Conditions:
with hydrazine hydrate in butan-1-ol at 120; for 4 h;
Steps:
1.3.1. Synthesis of 6-bromo-1H-indazole-3-amine (11)
A mixture of 4-bromo-2-fluorobenzonitrile 10 (6.00 g, 30.0 mmol) and 80% hydrazine hydrate (2.32 mL, 60.0 mmol) in n-butanol (25 mL) was heated at 120 for 4 h. After reactant consumed completely, the precipitate that formed was filtered, washed with appropriate n-heptane for twice, and dried in vacuum to obtain the desired product 11 as a white solid powder (5.93 g, 94%). 1H NMR (600 MHz, DMSO-d6) δ 11.50 (s, 1 H), 7.65 (d, J = 9.0 Hz, 1 H), 7.42 (s, 1 H), 7.03 (d, J = 8.4 Hz, 1 H), 5.46 (s, 2 H).
References:
Wang, Xing-Rong;Wang, Shuai;Li, Wen-Bo;Xu, Kai-Yan;Qiao, Xue-Peng;Jing, Xue-Li;Wang, Zi-Xiao;Yang, Chang-jiang;Chen, Shi-Wu [European Journal of Medicinal Chemistry,2021,vol. 213,art. no. 113192] Location in patent:supporting information