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tert-Butyl 4-bromo-3-cyano-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate

  • CAS No. 1333996-55-6

  • Cat. No. CS-0137757
  • Purity≥97%
  • MDL No.MFCD22627996

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

tert-Butyl 4-bromo-3-cyano-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate|CS-0137757

Structure of 1333996-55-6

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General Information

  • CAS No. 1333996-55-6
  • Cat. No. CS-0137757
  • Purity ≥97%
  • MDL No. MFCD22627996
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₆BrN₃O₂
  • Molecular Weight 338.20
  • Synonym(s) tert-butyl 4-bromo-3-cyano-6,8-dihydro-5H-1,7-naphthyridine-7-carboxylate
  • SMILES O=C(N1CCC2=C(N=CC(C#N)=C2Br)C1)OC(C)(C)C

Description

tert-Butyl 4-bromo-3-cyano-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate features a sterically shielded tert-butyl ester and a bromo-substituted naphthyridine core, enabling direct functionalization in late-stage diversification. The electron-deficient ring system supports palladium-catalyzed cross-coupling reactions under standard conditions. This bench-stable intermediate integrates readily into complex heterocyclic architectures for medicinal chemistry applications.

Application

tert-Butyl 4-bromo-3-cyano-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate serves as a versatile building block for the synthesis of functionalized naphthyridine scaffolds. The bromo and cyano groups enable palladium-catalyzed cross-coupling and nucleophilic substitution reactions, respectively, while the tert-butyl ester facilitates selective deprotection under mild acidic conditions. Its stability and compatibility with standard synthetic protocols make it well-suited for medicinal chemistry and process development workflows.

Safety Information

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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   66.22
  • LogP   3.00898
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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