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Chemical Structure| 925677-89-0 Chemical Structure| 925677-89-0

Structure of 925677-89-0

Chemical Structure| 925677-89-0

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Product Details of [ 925677-89-0 ]

CAS No. :925677-89-0
Formula : C10H8FN3
M.W : 189.19
SMILES Code : NC1=NC(C2=CC=CC(F)=C2)=CN=C1
MDL No. :MFCD12033125

Safety of [ 925677-89-0 ]

Application In Synthesis of [ 925677-89-0 ]

* 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 [ 925677-89-0 ]

[ 925677-89-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 768-35-4 ]
  • [ 33332-28-4 ]
  • [ 925677-89-0 ]
YieldReaction ConditionsOperation in experiment
95% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 110℃; for 4h; 6-(3-Fluorophenyl)pyrazin-2-amine To a stirred solution of <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (2.0 g, 15.43 mmol) in a mixture of toluene (90 ml.) and ethanol (8.5 ml_) was added 3-fluorophenyl boronic acid (2.60 g, 18.51 mmol) and a 2M aqueous solution of sodium carbonate (16.2 mL, 32.40 mmol). The mixture was subjected to three cycles of evacuation-backfilling with argon, and tetrakis(triphenylphosphine)palladium (0.713 g, 0.617 mmol) was added. The mixture was subjected again to three cycles of evacuation-backfilling with argon the flask was capped and placed in a 11O0C oil bath. After 4h, the mixture was cooled, partitioned between dichloromethane and water the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (33percent ethyl acetate in hexanes to 50percent ethyl acetate in hexanes). Concentration in vaccuo of the product-rich fractions provided the titled compound (2.79 g, 95percent) as a yellowish solid (2.79 g, 95percent). delta 1H-NMR (CDCI3): 8.38 (s, 1 H), 7.95 (s, 1H), 7.60 (m, 2H), 7.40 (m, 1 H), 4.65 (s, 2H).
  • 2
  • [ 925677-89-0 ]
  • [ 458532-98-4 ]
  • 5-(3-chloropyridin-4-yl)-6-(3-fluorophenyl)pyrazin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.166667h; 5-(3-Chloropyridin-4-yl)-6-(3-fluorophenyl)pyrazin-2-amine A microwave oven reactor was charged with 5-bromo-6-(3-fluorophenyl)pyrazin-2-amine (Preparation 1 , 0.3 g, 1.11 mmol), <strong>[458532-98-4](3-chloropyridin-4-yl)boronic acid</strong> (212 mg, 1.03 mmol), [1 ,1'-bis(diphenylphosphino)ferrocene] palladium(ll)dichloride dichloromethane complex (1:1) (39 mg, 0.047 mmol), dioxane (8 ml_) and a 1.2M aqueous solution of cesium carbonate was added (1.9 ml_, 2.39 mmol). The mixture was heated to 15O0C for 10min in the microwave oven, then cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane to dichloromethane/methanol 90:10) furnished the title compound as a yellowish solid (78 mg, 39%). delta 1H-NMR (CDCI3): 8.55 (s, 1 H)1 8.45 (d, 1H), 8.05 (s, 1H), 7.30 (d, 1H), 7.15 (m,2H), 7.00 (m, 2H), 4.85 (bs, 2H).ESI/MS m/e: 301 ([M+H] C15H10CIFN4) Retention time (min.): 12
 

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