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CS-W001157 4
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4-Chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine

  • CAS No. 1015610-31-7

  • Cat. No. CS-B0562
  • Purity≥97%
  • MDL No.MFCD09965886

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

4-Chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine|CS-B0562

Structure of 1015610-31-7

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General Information

  • CAS No. 1015610-31-7
  • Cat. No. CS-B0562
  • Purity ≥97%
  • MDL No. MFCD09965886
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄ClIN₂
  • Molecular Weight 278.48
  • Synonym(s) 4-Chloro-5-iodo-7-azaindole
  • SMILES ClC1=C2C(NC=C2)=NC=C1I

Description

4-Chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine is a halogenated heterocycle featuring complementary reactive sites for cross-coupling. The chlorine and iodine substituents enable sequential functionalization under palladium catalysis. This scaffold integrates readily into complex molecular architectures with defined regiochemistry.

Application

4-Chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine serves as a versatile building block for constructing biologically relevant heterocycles via palladium-catalyzed cross-coupling reactions. The ortho-halogen substitution pattern enables sequential functionalization, with the chloro group participating in Suzuki-Miyaura or Buchwald-Hartwig couplings, while the iodo moiety offers high reactivity in Stille and Negishi transformations. Bench-stable and amenable to purification by flash chromatography, it facilitates efficient access to complex pyrrolopyridine scaffolds in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • ARRAY BIOPHARMA INC. Patent: WO2009/140320 A1, 2009 ; Location in patent: Page/Page column 98 ; WO 2009/140320 A1
  • Route2
    • 4-chloro-5-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine|CS-0005221
      1015609-83-2
    • ~99%
    • In-stock
      4-Chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine|CS-B0562
      1015610-31-7

    References

    • Heinrich, Timo; Seenisamy, Jeyaprakashnarayanan; Emmanuvel, Lourdusamy; Kulkarni, Santosh S.; Bomke, Joerg; Rohdich, Felix; Greiner, Hartmut; Esdar, Christina; Krier, Mireille; Graedler, Ulrich; Musil, Djordje Journal of Medicinal Chemistry, 2013 , vol. 56, # 3 p. 1160 - 1170
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 56, # 3 p. 1160 - 1170

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   28.68
  • LogP   2.8209
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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