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Chemical Structure| 1142189-49-8 Chemical Structure| 1142189-49-8

Structure of 1142189-49-8

Chemical Structure| 1142189-49-8

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Product Details of [ 1142189-49-8 ]

CAS No. :1142189-49-8
Formula : C9H9BrN2
M.W : 225.09
SMILES Code : CC1=C2C=CC(Br)=CC2=NN1C
MDL No. :MFCD11869881
InChI Key :OAYUNSJKNKZYHT-UHFFFAOYSA-N
Pubchem ID :44119470

Safety of [ 1142189-49-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1142189-49-8 ]

* 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 [ 1142189-49-8 ]

[ 1142189-49-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 7746-27-2 ]
  • [ 74-88-4 ]
  • [ 1095539-84-6 ]
  • [ 1142189-49-8 ]
YieldReaction ConditionsOperation in experiment
Intermediate 114 6-bromo-1,3-dimethyl-1H-indazole(a) and 6-bromo-2,3-dimethyl-2H-indazole(b) To a solution of intermediate 95 (2 g, 9.47 mmoles) in THF (30 ml) cooled to 0 C., sodium hydride (0.454 g, 60% in paraffin oil, 11.37 mmoles) was added and stirred for 10 min. Methyl iodide (2.0 gl, 14.21 mmoles) was added warmed to room temperature. After 12 h, the reaction mixture cooled to room temperature, quenched with water, extracted with ethyl acetate and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as colourless solid. Fraction I (114a, 0.90 g, 43% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 7.87 (d, J=1.0 Hz, 1H), 7.64 (d, J=9.5 Hz, 1H), 7.20 (dd, J=9.5, 1.5 Hz, 1H), 3.92 (s, 3H), 2.44 (s, 3H). Fraction II (114b, 0.80 g, 38% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 7.72 (d, J=1.3 Hz, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.20 (dd, J=8.8, 1.6 Hz, 1H), 4.01 (s, 3H), 2.58 (s, 3H).
[0001206] To 6-bromo-3 -methyl- lH-indazole (1.9 g, 9.05 mmol) in DMF (15 mL) was added sodium hydride (60% in mineral, 398 mg, 9.96 mmol) with ice bath cooling. The mixture was stirred for 30 min at room temperature and iodomethane (0.94 mL, 27.15 mmol) was added. The reaction mixture was stirred at room temperature for 3 h, quenched with ammonium chloride solution (30 mL), and extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 90% v/v) to give Compound 340A and Compound 340B.
  • 2
  • [ 7746-27-2 ]
  • methyl halide [ No CAS ]
  • [ 1095539-84-6 ]
  • [ 1142189-49-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 150℃; under 760.051 Torr; for 0.416667h;Microwave irradiation; General procedure: In a 5 ml. microwave vial, was added 6~bromo~3-methyl-l.H-.itidazoie (Icq). CESIUM CARBONATE- (534-17-8) (2eq), DMF (0.2M) and alkyi halide (1.5eq). The txa was heated to I5 C m the microwave for 25 mm. The rxn was added to EtOAe; water ( 1 :1), The organic layer was separated aod washed with water (2x), brine and dried (MgSO). After filtration, the solvent was removed under reduced pressure. Purification on normal phase chromatography (Biotage; 5-30% EtOAe hexanes) to provide 6-bromo~3-mediyi- l -alky-indazole (64% yield) and 6-bromo-3-methyl-2-alkyl-indazok (23% yield).
  • 3
  • [ 1142189-49-8 ]
  • [ 593-51-1 ]
  • [ 1376676-65-1 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydrogencarbonate; In ethanol; at 75 - 78℃; for 4h; Add 22.5g (0.1mol) 6-bromo-2,3-dimethyl-2H-indazole and 400ml ethanol to a 1L reaction flask, stir add 10.1g (0.15mol) monomethylamine hydrochloride, add 25.2g ( 0.3 mol) sodium bicarbonate, the temperature is raised to 75-78C, and the reaction is carried out for 4 hours. Cool to room temperature, filter the resulting reaction solution, concentrate the mother liquor, add 200 mL ethyl acetate and 200 mL water, stir and separate the layers, and then extract the aqueous layer twice with 200 mL ethyl acetate, each with 100 mL, combine the ethyl acetate layers, reduce press and concentrate to dryness. The obtained residue was recrystallized by adding 120 mL of ethyl acetate to obtain 15.8 g of off-white solid with a molar yield of 90%.
  • 4
  • [ 1142189-49-8 ]
  • [ 74-89-5 ]
  • [ 1376676-65-1 ]
YieldReaction ConditionsOperation in experiment
97% With copper(I) oxide; In N,N-dimethyl-formamide; at 100℃; A flask was charged with 6-bromo-2,3-dimethyl-2H-indazole (1 eq.), methylamine (2 eq.), CU2O (5 mol%) and Ν,Ν-dimethylformamide. The reaction mixture was stirred at 100 C until completion of the reaction. Then, the reaction mixture was cooled to room temperature and water was added. The mixture was extracted with dichloromethane. Organic layer was separated and dried with anhydrous sodium sulfate. The solvent was removed in vacuo to obtain oily residue. Diethyl ether was added onto the oily residue and stirred for 2 h for crystallization. Product crystals were collected by filtration, washed with diethyl ether and dried to afford a brownish powder (Yield: 97%; LC-purity: 99%).
 

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[ 1142189-49-8 ]

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Related Parent Nucleus of
[ 1142189-49-8 ]

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