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Chemical Structure| 3430-18-0 Chemical Structure| 3430-18-0
Chemical Structure| 3430-18-0

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CAS No.: 3430-18-0

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Product Details of [ 3430-18-0 ]

CAS No. :3430-18-0
Formula : C6H5Br2N
M.W : 250.92
SMILES Code : C1=C(Br)C=NC(=C1C)Br
MDL No. :MFCD02093085
InChI Key :LIMXEVCFAUTBCK-UHFFFAOYSA-N
Pubchem ID :817680

Safety of [ 3430-18-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H315-H318
Precautionary Statements:P280-P301+P310-P305+P351+P338
Class:8(6.1)
UN#:2923
Packing Group:Ⅲ

Application In Synthesis [ 3430-18-0 ]

* 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 [ 3430-18-0 ]

[ 3430-18-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 4394-85-8 ]
  • [ 3430-18-0 ]
  • [ 885167-81-7 ]
YieldReaction ConditionsOperation in experiment
74% Method 4; Preparation of 6-bromo-5-methylnicotinaldehyde; 2,5-Dibromo-3-picoline (5.1 g, 20.30 mmol) in tetrahydrofuran (25 ml) was added dropwise to a 2M solution of isopropylmagnesium chloride (10.7 ml, 21.3 mmol) in tetrahydrofuran at 0 C. The solution was stirred for 2 hours at 0 C. and then for 1 hour at ambient temperature. A solution of 4-formylmorpholine (2.1 ml, 20.3 mmol) in tetrahydrofuran (25 ml) was added dropwise and the solution stirred at ambient temperature for 1 hour. The solution was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulphate, filtered and the solution concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with 10% ethyl acetate in isohexane, to give the title compound (3.0 g, 74%); NMR Spectrum: (DMSO-d6) 2.44 (s, 3H), 8.19 (s, 1H), 8.73 (s, 1H), 10.09 (s, 1H).
74% Method 3; Preparation of 6-bromo-5-methvmicotmaldehvde; 2,5-Dibromo-3-picoline (5.1 g, 20.30 mmol) in tetrahydrofuran (25 ml) was added dropwise to a 2M solution of isopropylmagnesium chloride (10.7 ml, 21.3 mmol) in tetrahydrofuran at 0 0C. The solution was stirred for 2 hours at 0 0C and then for 1 hour at ambient temperature. A solution of 4-formylmorpholine (2.1 ml, 20.3 mmol) in tetrahydrofuran (25 ml) was added dropwise and the solution stirred at ambient temperature for 1 hour. The solution was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulphate, filtered and the solution concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with 10 % ethyl acetate in isohexane, to give the title compound (3.0 g, 74 %); NMR Spectrum: (DMSO-d6) 2.44 (s, 3H), 8.19 (s, IH), 8.73 (s, IH), 10.09 (s, IH).
Under an argon atmosphere, a solution of 2 M isopropylmagnesium chloride in THF (5.5 ml) was cooled to -78 C., and a solution of 2,5-dibromo-3-methylpyridine (2.5 g) in THF (10 ml) was added dropwise. After stirring at the same temperature for 30 minutes, a solution of morpholine-4-carboaldehyde (1.26 g) in THF (5 ml) was added dropwise thereto, followed by elevating the temperature to 0 C. over 30 minutes, followed by stirring at 0 C. for 2 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 6-bromo-5-methyl nicotine aldehyde (1.42 g).
  • 2
  • [ 3430-18-0 ]
  • [ 151169-74-3 ]
  • 5-bromo-2-(2,3-dichlorophenyl)-3-methylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With palladium diacetate; potassium carbonate; triphenylphosphine; In methanol; acetonitrile; at 50℃; for 24h;Inert atmosphere; A mixture of 2,5-dibromo-3-methylpyridine (5.0 g, 19.93 mmol), (2,3- dichlorophenyl)boronic acid (4.2 g, 21.92 mmol), Pd(OAc)2 (447 mg, 1.99 mmol), PPh3 (1.1 g, 3.99 mmol), and K2C03 (5.5 g, 39.86 mmol) in CH3CN (150 mL) and MeOH (75 mL) was stirred at 50 C under nitrogen atmosphere for 24 hrs. The reaction mixture was poured into 50 mL of H20 and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford 5-bromo-2-(2,3-dichlorophenyl)-3-methylpyridine (5.1 g, 81 % yield) as a light yellow oil. ‘H NIVIR (400 MHz, Chloroform-cl) ppm 8.57 (d, J=9.21 Hz, 1 H) 7.76 (d, J=8.77 Hz, 1 H) 7.52 (t, J=8.33 Hz, 1 H) 7.35 -7.25 (m, 1 H) 7.23 - 7.15 (m, 1 H) 2.13 (d, J9.21 Hz, 3H).
 

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