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Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate

  • CAS No. 87597-21-5

  • Cat. No. CS-0102752
  • Purity≥95%
  • MDL No.MFCD14706101

*For research and further manufacturing use only, not for direct human use.

Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate|CS-0102752

Structure of 87597-21-5

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General Information

  • CAS No. 87597-21-5
  • Cat. No. CS-0102752
  • Purity ≥95%
  • MDL No. MFCD14706101
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇Br₂N₃O₂
  • Molecular Weight 348.98
  • Synonym(s) Imidazo[1,2-a]pyrazine-2-carboxylic acid, 6,8-dibromo-, ethyl ester
  • SMILES O=C(C1=CN2C(C(Br)=NC(Br)=C2)=N1)OCC

Description

Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate is a sterically hindered, electron-deficient heterocyclic scaffold featuring two bromine substituents at the 6 and 8 positions. This configuration enhances its utility in palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation under standard conditions. The ester functionality provides synthetic handle for further derivatization.

Application

Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate serves as a versatile building block for constructing brominated heterocyclic scaffolds in medicinal chemistry. The dibromo substitution enables sequential cross-coupling reactions, while the ester group facilitates further functionalization. Its bench-stable nature and compatibility with palladium-catalyzed transformations make it well-suited for modular synthesis of complex imidazo[1,2-a]pyrazine derivatives used in target-oriented drug discovery.

Synthesis

  • Route1
    • null|null
      70-23-5
    • In-stock
      Amino-3,5-dibromopyrazine|CS-D1346
      24241-18-7
    • ~52%
    • In-stock
      Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate|CS-0102752
      87597-21-5

    References

    • BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard Patent: WO2012/80234 A1, 2012 ; Location in patent: Page/Page column 45 ; WO 2012/080234 A1
  • Route2
    • null|null
      65868-37-3
    • In-stock
      Amino-3,5-dibromopyrazine|CS-D1346
      24241-18-7
    • ~%
    • In-stock
      Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate|CS-0102752
      87597-21-5

    References

    • Sablayrolles; Cros; Milhavet; Rechenq; Chapat; Boucard; Serrano; McNeill Journal of Medicinal Chemistry, 1984 , vol. 27, # 2 p. 206 - 212

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   56.49
  • LogP   2.431
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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