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tert-Butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

  • CAS No. 168824-94-0

  • Cat. No. CS-D1079
  • Purity≥98%
  • MDL No.MFCD09029520

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

tert-Butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate|CS-D1079

Structure of 168824-94-0

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General Information

  • CAS No. 168824-94-0
  • Cat. No. CS-D1079
  • Purity ≥98%
  • MDL No. MFCD09029520
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₀N₂O₂
  • Molecular Weight 272.34
  • Synonym(s) tert-butyl 1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
  • SMILES O=C(N(C1)CCC2=C1NC3=C2C=CC=C3)OC(C)(C)C

Description

tert-Butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate features a sterically protected carbamate group that enables stable handling and straightforward deprotection under mild acidic conditions. The fused pyridoindole core offers enhanced planarity and electron-rich character, facilitating integration into bioactive scaffolds for medicinal chemistry applications.

Application

tert-Butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate serves as a versatile scaffold for the synthesis of pyridoindole-based heterocycles, offering robust bench stability and compatibility with standard coupling reactions. The protected indole core enables selective functionalization at C3 and C4 positions, facilitating downstream derivatization in medicinal chemistry campaigns. Its tert-butyl ester group allows for straightforward deprotection under mild acidic conditions, supporting efficient access to bioactive analogs.

Synthesis

  • Route1

    References

    • Kikuchi, Chika; Ando, Takashi; Watanabe, Takashi; Nagaso, Hiroshi; Okuno, Masayo; Hiranuma, Toyokazu; Koyama, Masao Journal of Medicinal Chemistry, 2002 , vol. 45, # 11 p. 2197 - 2206
  • Route2

    References

    • Jana, Navendu; Nguyen, Quyen; Driver, Tom G. Journal of Organic Chemistry, 2014 , vol. 79, # 6 p. 2781 - 2791
  • Route3
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      615-36-1
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    • In-stock
      tert-Butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate|CS-D1079
      168824-94-0

    References

    • Jana, Navendu; Nguyen, Quyen; Driver, Tom G. Journal of Organic Chemistry, 2014 , vol. 79, # 6 p. 2781 - 2791

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   45.33
  • LogP   3.4611
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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