ChemicalBook CAS DataBase List 6-Iodo-1H-indazole

6-Iodo-1H-indazole synthesis

5synthesis methods

Product Name:6-Iodo-1H-indazole
CAS Number:261953-36-0
Molecular formula:C7H5IN2
Molecular Weight:244.03

Revill P. and co-worker synthesized Axitinib by iodination of 6-iodo-1H-indazole (100) to give 3,6-di iodo- 1H-indazole (101) ,which on further reaction with 2- mercapto-N-methylbenzenesulfinamide gives 2-(3-iodo-1Hindazol-6-ylthio)-N-methylbenzamide (101), the same can be obtained via 2-(1H-indazol-6-ylthion)-N-methylbenzamide (102) starting from 6-iodo-1H-indazole (100) through alternative route. N-protection of 2-(3-iodo-1H-indazol-6- ylthio)-N-methylbenzamide (101) by Boc2, DMAP or DHP, TsOH gives respective N-protected intermediates 103, 104. Further treatment of 103, 104 with 2-vinyl pyridine give rise to N-protected-2-(1-methyl-3-(2-(pyridine-2-yl) vinyl)-1Hindazole-6-ylthio) benzothioamide 105 and 106. Deprotection of 105 and 106 gives destination compound axitinib (107), the same can be obtained without protection from 2-(3-iodo-1H-indazol-6-ylthio)-N-methylbenzamide (101) by simple reaction with 2-vinyl pyridine^[1].

79762-54-2 Synthesis

79762-54-2
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$3.00/1g

261953-36-0
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$9.00/250mg

Yield:261953-36-0 85%

Reaction Conditions:

with copper(l) iodide;tetra-(n-butyl)ammonium iodide;N,N-dimethylethylenediamine;potassium iodide in 1,4-dioxane for 48 h;Reflux;Reagent/catalyst;Solvent;

Steps:

1 Example 1 A method of synthesizing 6-iodo -1H- indazole, the following synthetic route:
The method of synthesizing the above-described 6-iodo-1H-indazole, comprising the steps of: Weigh 5.0 g of the compound of formula V and 13.38 g of potassium iodide in the reactor.After adding 50 mL of 1,4-dioxane, 0.2 g of tetrabutylammonium iodide was added, based on the compound of formula V.0.51 g of cuprous iodide and 0.47 g of N,N-dimethylethylenediamine (0.2 equiv.) were added to the reactor, the temperature was raised to reflux, and the reaction was refluxed for 48 h.After the reaction was completed, after cooling to room temperature, the reaction solution was filtered, and the filter cake was washed three times with 1,4-dioxane.The filtrate was combined, and the obtained filtrate was concentrated. After the concentrate was dissolved in ethyl acetate, ethyl acetate layer was washed with 13% aqueous ammonia.The organic phase is separated, the organic phase is concentrated, and the concentrate is recrystallized from acetonitrile.To give compound of formula 6-iodo-1H-indazole in 85% yield,

References:

Anhui Nuoquan Pharmaceutical Co., Ltd.;Qian Zhujin;Hu Zhigang;Xu Liangzhi;He Darong;Du Xiaopeng;He Yong;Chen Yuelei CN109761904, 2019, A Location in patent:Paragraph 0027-0046; 0050; 0051

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6967-12-0 Synthesis