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tert-Butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate

  • CAS No. 459133-68-7

  • Cat. No. CS-0088492
  • Purity≥98%
  • MDL No.MFCD09056828

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

tert-Butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate|CS-0088492

Structure of 459133-68-7

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General Information

  • CAS No. 459133-68-7
  • Cat. No. CS-0088492
  • Purity ≥98%
  • MDL No. MFCD09056828
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₂BrIN₂O₂
  • Molecular Weight 423.04
  • Synonym(s) 1-Boc-5-Bromo-3-iodo-1H-indazole
  • SMILES O=C(N1N=C(I)C2=C1C=CC(Br)=C2)OC(C)(C)C

Description

tert-Butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate features a dual halogenated indazole core with orthogonal reactivity, enabling sequential cross-coupling strategies. The tert-butyl ester provides enhanced stability and solubility in organic media, simplifying purification. This compound serves as a key scaffold for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Application

tert-Butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate serves as a versatile building block for the synthesis of functionalized indazole scaffolds. The molecule enables sequential cross-coupling reactions due to its complementary halogenation pattern, with bromo and iodo groups facilitating Pd-catalyzed couplings under standard conditions. Its tert-butyl ester group offers stability and ease of removal during late-stage functionalization. This compound is well-suited for medicinal chemistry campaigns requiring precise substitution control on the indazole core.

Synthesis

  • Route1

    References

    • MERCK SHARP and DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; HABERMANN, Joerg; KOCH, Uwe; NARJES, Frank; LI, Peng; PENG, Xuanjia; SOLL, Richard; WU, Hao; PALANI, Anandan; DAI, Xing; LIU, Hong; HE, Shuwen; DANG, Qung Patent: WO2013/34048 A1, 2013 ; Location in patent: Page/Page column 58 ;
  • Route2

    References

    • ABBOTT LABORATORIES Patent: WO2008/154241 A1, 2008 ; Location in patent: Page/Page column 75 ;
  • Route3

    References

    • Arnautu, Anca; Collot, Valerie; Ros, Javier Calvo; Alayrac, Carole; Witulski, Bernhard; Rault, Sylvain Tetrahedron Letters, 2002 , vol. 43, # 15 p. 2695 - 2697

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361-P405-P501

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Computational Chemistry Data

  • TPSA   44.12
  • LogP   4.1866
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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