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Chemical Structure| 79762-54-2

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Product Details of 6-Bromo-1H-indazole

CAS No. :79762-54-2
Formula : C7H5BrN2
M.W : 197.03
SMILES Code : BrC1=CC=C2C(=C1)[NH]N=C2
MDL No. :MFCD03265457
InChI Key :WMKDUJVLNZANRN-UHFFFAOYSA-N
Pubchem ID :17842471

Safety of 6-Bromo-1H-indazole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 6-Bromo-1H-indazole

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 79762-54-2 ]

[ 79762-54-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 79762-54-2 ]
  • [ 78191-00-1 ]
  • [ 189559-85-1 ]
YieldReaction ConditionsOperation in experiment
9% A. l-(lH-indazol-6-yl)ethanone (24-a) [00303] To a solution of 6-bromo-lH-indazole (5.0 g, 25.4 mmol) in 40 mL THF was added dropwise n-BuLi (2.5M, 30mL, 76.2 mmol) at -65 C, and the mixture was stirred for 2 h. Then, N-methoxy-N-methylacetamide (2.9 g, 27.9 mmol) was added. The reaction mixture was stirred for another 2 h at -65 C, then quenched with 40 mL H20. The mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with 100 mL brine, dried, and concentrated to dryness. The residue was purified by flash column chromatography (PE/EA=40/1) to give the title compound 24-a (370 mg, 9%) as a yellow solid. [M+H] Calc'd for C9H8N20, 161; Found, 161.
  • 2
  • [ 79762-54-2 ]
  • [ 83004-13-1 ]
  • 6-bromo-2-(6-methylpyridin-2-yl)-2H-indazole [ No CAS ]
  • 6-bromo-1-(6-ethylpyridin-2-yl)-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
19%; 26% The preparation of 6-bromo-l-(6-ethylpyridin-2-yl)-lH-indazole was the same as that of 6-bromo-l-(6-methylpyridin-2-yl)-lH-indazole. The mixture of 6-bromo-l-(6- ethylpyridin-2-yl)-lH-indazole and 6-bromo-2-(6-ethylpyridin-2-yl)-2H-indazole was purified by pre-TLC (PE/EA = 10/1) to give 41-02-0002 and 6-bromo-2-(6-ethylpyridin-2- yl)-2H-indazole. Rf value of 6-bromo-l-(6-ethylpyridin-2-yl)-lH-indazole is more than that of 6-bromo-2-(6-ethylpyridin-2-yl)-2H-indazole. 6-bromo-l-(6-ethylpyridin-2-yl)-lH-indazole, 230 mg, as a yellow solid, Y: 26percent. ESI-MS (M+H)+: 302.0, 304.0. 6-bromo-2-(6-ethylpyridin-2-yl)-2H-indazole, 170 mg, as a yellow solid, Y: 19percent. ESI-MS (M+H)+: 302.0, 304.0.
  • 3
  • [ 79762-54-2 ]
  • [ 1037223-35-0 ]
  • 6-bromo-1-(6-isopropylpyridin-2-yl)-1H-indazole [ No CAS ]
  • 6-bromo-2-(6-isopropylpyridin-2-yl)-2H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
23%; 21% The preparation of 6-bromo-l-(6-isopropylpyridin-2-yl)-lH-indazole was the same as that of 6-bromo-l-(6-methylpyridin-2-yl)-lH-indazole. The mixture of 6-bromo-l-(6- isopropylpyridin-2-yl)-lH-indazole and 6-bromo-2-(6-isopropylpyridin-2-yl)-2H-indazole was purified by pre-TLC (PE/EA = 10/1) to give 6-bromo-l-(6-isopropylpyridin-2-yl)-lH- indazoleand 6-bromo-2-(6-isopropylpyridin-2-yl)-2H-indazole. Rf value of 6-bromo-l-(6- isopropylpyridin-2-yl)-lH-indazole is more than that of 6-bromo-2-(6-isopropylpyridin-2-yl)- 2H-indazole. 6-bromo-l-(6-isopropylpyridin-2-yl)-lH-indazole, 200 mg, as a yellow solid, Y: 23%. ESI-MS (M+H)+: 316.0, 318.0. 6-bromo-2-(6-isopropylpyridin-2-yl)-2H-indazole, 180 mg, as a yellow solid, ESI-MS (M+H)+: 316.0, 318.0.
  • 4
  • [ 79762-54-2 ]
  • [ 1083326-75-3 ]
  • N-(5-(1H-indazol-6-yl)-2-methoxypyridin-3-yl)methanesulfonamide [ No CAS ]
  • 5
  • [ 79762-54-2 ]
  • [ 5722-11-2 ]
  • 1-(1H-indazol-6-yl)-2,2-dimethylcyclopropane-1-carbonitrile [ No CAS ]
  • 6
  • [ 79762-54-2 ]
  • [ 261953-36-0 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; tetra-(n-butyl)ammonium iodide; N,N-dimethylethylenediamine; potassium iodide; In 1,4-dioxane; for 48h;Reflux; 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,
 

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