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Chemical Structure| 18813-71-3 Chemical Structure| 18813-71-3

Structure of 18813-71-3

Chemical Structure| 18813-71-3

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Product Details of [ 18813-71-3 ]

CAS No. :18813-71-3
Formula : C12H9BrN2
M.W : 261.12
SMILES Code : CC1=NC=CC2=C1NC3=C2C=C(Br)C=C3

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Application In Synthesis of [ 18813-71-3 ]

* 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 [ 18813-71-3 ]

[ 18813-71-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 18813-71-3 ]
  • [ 199609-62-6 ]
  • [ 1374752-45-0 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 90℃; for 2h;Inert atmosphere; 6-bromoharmane (635 mg, 2.43 mmol) and 3-(N-Boc)-aminomethylphenyl boronic acid (732 mg, 2.92 mmol) were combined in deoxygenated dioxane (30 mL).A potassium phosphate solution (1.55 g, 7.29 mmol in 6 mL deoxygenated water) was added to the reaction mixture. The reaction mixture was stirred rapidly under argon. PdCl2dppf (177.8 mg, 0:243 mmol) was then added and the reaction mixture transferred to a pre-heated oil bath and stirred rapidly under argon at 90C. After 2 hours TLC, analysis indicated that all starting material had been consumed.The reaction was allowed to cool to room temperature and diluted with ethyl acetate (100 mL). This mixture was filtered through celite and washed with additional ethyl acetate. The organics were washed with water and twice with brine, dried over MgS04 and filtered and the solvent removed under reduced pressure. The residue was purified over silica (1 : 1 heptane/ethyl acetate to 10 % methanol / ethyl acetate) to give N-Boc-(3-(l -methyl-9H-pyrido[3,4-b]indol-6-yl)phenyl)methanamine (780 mg, 2.02 mmol), which was then dissolved in dioxane (10 mL). 4N HC1 in dioxane (50 mL) was added to this solution and the reaction mixture was stirred at room temperature. After 30 minutes, a thick yellow precipitate was formed and was then collected by suction filtration, washed with dioxane and dried in a vacuum oven to give (3-(l -methyl-9H-pyrido[3,4-b]indol-6-yl)phenyl)methanamine (710 mg).(3-(l -methyl-9H-pyrido[3,4-b]indol-6-yl)phenyl)methanamine (50 mg, 0.17 mmol) was suspended in dichloromethane (4 mL) and DIPEA (91 μ, 0.52 mmol) at room temperature. The respective isocyanate was added to this mixture and the reactions stirred at room temperature for 1 hour. A precipitate was formed and was collected by suction filtration to give the desired products.The following compounds were prepared using this procedure:l -ethyl-3-(3-(l-methyl-9H-pyrido[3,4-b]indol-6-yl)benzyl)urea (E41 ; 31 mg)
 

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