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tert-Butyl 4-[(trifluoromethyl)sulfonyloxy]-5,6-dihydropyridine-1(2H)-carboxylate

  • CAS No. 138647-49-1

  • Cat. No. CS-W019633
  • Purity≥95%
  • MDL No.MFCD09997858

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

tert-Butyl 4-[(trifluoromethyl)sulfonyloxy]-5,6-dihydropyridine-1(2H)-carboxylate|CS-W019633

Structure of 138647-49-1

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General Information

  • CAS No. 138647-49-1
  • Cat. No. CS-W019633
  • Purity ≥95%
  • MDL No. MFCD09997858
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₆F₃NO₅S
  • Molecular Weight 331.31
  • Synonym(s) tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate
  • SMILES O=S(C(F)(F)F)(OC1=CCN(CC1)C(OC(C)(C)C)=O)=O

Description

tert-Butyl 4-[(trifluoromethyl)sulfonyloxy]-5,6-dihydropyridine-1(2H)-carboxylate features a triflate leaving group positioned ortho to a dihydropyridine core, enabling efficient palladium-catalyzed cross-coupling reactions. This bench-stable reagent integrates readily into synthetic sequences requiring selective C–H functionalization or heterocyclic diversification under mild conditions.

Application

tert-Butyl 4-[(trifluoromethyl)sulfonyloxy]-5,6-dihydropyridine-1(2H)-carboxylate serves as a versatile building block for the construction of functionalized pyridine scaffolds. The triflate group enables efficient late-stage diversification via palladium-catalyzed cross-coupling reactions, while the dihydropyridine core offers controlled reactivity for selective transformations. Bench-stable and compatible with standard synthetic workflows, it facilitates rapid access to substituted heterocycles relevant in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2007/60409 A1, 2007 ; Location in patent: Page/Page column 87-88 ; WO 2007/060409 A1
  • Route2

    References

    • INCYTE CORPORATION Patent: WO2005/37826 A1, 2005 ; Location in patent: Page/Page column 90 ; WO 2005/037826 A1
  • Route3
    • In-stock
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      37595-74-7
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      79099-07-3
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    • In-stock
      tert-Butyl 4-[(trifluoromethyl)sulfonyloxy]-5,6-dihydropyridine-1(2H)-carboxylate|CS-W019633
      138647-49-1

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; BENTZIEN, Joerg, Martin; BOYER, Stephen, James; BURKE, Jennifer; ELDRUP, Anne, Bettina; GUO, Xin; HUBER, John, David; KIRRANE, Thomas, Martin; SOLEYMANZADEH, Fariba; SWINAMER, Alan, David Patent: WO2010/5783 A1, 2010 ; Location in patent: Page/Page column 115 ; WO 2010/005783 A1

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

Quality Control

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Computational Chemistry Data

  • TPSA   72.91
  • LogP   2.3773
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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