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CS-W001157 4
Total: USD 88.00

tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

  • CAS No. 400777-00-6

  • Cat. No. CS-W007089
  • Purity≥97%
  • MDL No.MFCD11977418

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

tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate|CS-W007089

Structure of 400777-00-6

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General Information

  • CAS No. 400777-00-6
  • Cat. No. CS-W007089
  • Purity ≥97%
  • MDL No. MFCD11977418
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂ClIN₂O₂
  • Molecular Weight 354.57
  • Synonym(s) Carbamicacid, N-(6-chloro-4-iodo-3-pyridinyl)-, 1,1-dimethylethyl ester
  • SMILES O=C(OC(C)(C)C)NC1=C(I)C=C(Cl)N=C1

Description

tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate serves as a pivotal building block in the synthesis of functionalized pyridine derivatives. The iodide moiety enables efficient late-stage diversification via palladium-catalyzed cross-coupling, while the tert-butoxycarbonyl group provides robust protection for the pyridinic nitrogen. This combination delivers enhanced stability and solubility under standard reaction conditions, streamlining access to complex heterocyclic architectures.

Application

tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable iodo functionality. The protected amine and orthogonal chloro substituent facilitate sequential functionalization, while the tert-butyl carbamate group offers bench stability and ease of removal under mild acidic conditions.

Synthesis

  • Route1

    References

    • Cooper, Laura C.; Chicchi, Gary G.; Dinnell, Kevin; Elliott, Jason M.; Hollingworth, Gregory J.; Kurtz, Marc M.; Locker, Karen L.; Morrison, Denise; Shaw, Duncan E.; Tsao, Kwei-Lan; Watt, Alan P.; Williams, Angela R.; Swain, Christopher J. Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 9 p. 1233 - 1236
  • Route2

    References

    • Cooper, Laura C.; Chicchi, Gary G.; Dinnell, Kevin; Elliott, Jason M.; Hollingworth, Gregory J.; Kurtz, Marc M.; Locker, Karen L.; Morrison, Denise; Shaw, Duncan E.; Tsao, Kwei-Lan; Watt, Alan P.; Williams, Angela R.; Swain, Christopher J. Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 9 p. 1233 - 1236
  • Route3

    References

    • Cooper, Laura C.; Chicchi, Gary G.; Dinnell, Kevin; Elliott, Jason M.; Hollingworth, Gregory J.; Kurtz, Marc M.; Locker, Karen L.; Morrison, Denise; Shaw, Duncan E.; Tsao, Kwei-Lan; Watt, Alan P.; Williams, Angela R.; Swain, Christopher J. Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 9 p. 1233 - 1236

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   51.22
  • LogP   3.6866
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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