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Chemical Structure| 1289387-96-7 Chemical Structure| 1289387-96-7

Structure of 1289387-96-7

Chemical Structure| 1289387-96-7

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Product Details of [ 1289387-96-7 ]

CAS No. :1289387-96-7
Formula : C7H8BrNO
M.W : 202.05
SMILES Code : COCC1=CC(Br)=NC=C1
English Name :2-Bromo-4-(methoxymethyl)pyridine
MDL No. :MFCD18837157
InChI Key :GIEVHFHVQIBIRQ-UHFFFAOYSA-N
Pubchem ID :53385534

Safety of [ 1289387-96-7 ]

Application In Synthesis of [ 1289387-96-7 ]

* 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 [ 1289387-96-7 ]

[ 1289387-96-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 118289-16-0 ]
  • [ 74-88-4 ]
  • [ 1289387-96-7 ]
YieldReaction ConditionsOperation in experiment
46.53% Stage #1: (2-bromopyridin-4-yl)methanol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 3h; 215 Synthesis of compound 215.3 To a solution of 215.2 (1.4g, 7.4mmol, l .Oeq) in tetrahydrofuran (15mL) at 0°C, sodium hydride (0.35g, 14.8mmol, 2.0eq) was added. Reaction mixture was stirred at 0°C for 20 min. Then, methyl iodide (1.57g, 11.2mmol, 1.5eq) was added. Reaction mixture was stirred at room temperature for 3h. After completion of reaction, reaction mixture was transferred in ice-water and product was extracted with ethyl acetate. Organic layer was combined, washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtain 215.3 (0.7g, 46.53%). MS(ES): m/z 203.58 [M]+
  • 2
  • [ 2222717-25-9 ]
  • [ 1289387-96-7 ]
  • [ 2222715-08-2 ]
YieldReaction ConditionsOperation in experiment
15.48% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 0.5h; Inert atmosphere; 215 Synthesis of VIII-17 To a solution of compound 215.3 (0.046g, 0.23mmol, 1.2eq) in 1,4-dioxane (lmL) was added 213.1 (0.080g, 0.19mmol, l .Oeq), cesium carbonate (0.187g, 0.57mmol, 3.0eq). The reaction mixture was degassed for 10 min. under argon atmosphere, then tris(dibenzylideneacetone)dipalladium(0) (0.017g, 0.019mmol, O. leq) and 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.027g, 0.037mmol, 0.2eq) were added, again degassed for 5 min. The reaction was stirred at 1 10°C for 30min. After completion of reaction, reaction mixture was cooled to room temperature, transferred in water and product was extracted with ethyl acetate. Organic layer was combined, washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography using 2% methanol in dichloromethane as eluant to obtain pure VIII-17 (0.016g, 15.48%). MS(ES): m/z 536.35 [M+H]+, LCMS purity : 96.59%, HPLC purity : 98.40%, NMR (CDCl3, 400MHZ): 10.84 (s, 1H), 9.91 (s, 1H), 8.55 (s, 1H), 8.16-8.15 (d, J=5.60Hz, 2H), 8.12 (s, 1H), 7.88-7.86 (d, J=7.6Hz, 1H), 7.67-7.65 (d, J=8.8Hz, 1H), 7.44 (s, 1H), 7.55 (s, 1H), 6.82 (s, 1H), 4.47 (s, 3H), 4.42 (s, 2H), 3.71 (s, 3H), 3.34 (s, 3H)
  • 3
  • [ 66572-56-3 ]
  • [ 1289387-96-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 3 h / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C 2.2: 3 h / 20 °C
 

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