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Ethyl 6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate

  • CAS No. 1121051-30-6

  • Cat. No. CS-0101666
  • Molecule weight337.09
  • Purity≥97%
  • MDL No.MFCD19704051

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

Ethyl 6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate|CS-0101666

Structure of 1121051-30-6

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General Information

  • CAS No. 1121051-30-6
  • Cat. No. CS-0101666
  • Purity ≥97%
  • MDL No. MFCD19704051
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈BrF₃N₂O₂
  • Molecular Weight 337.09
  • Synonym(s) Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-bromo-8-(trifluoromethyl)-, ethyl ester
  • SMILES O=C(OCC)C1=CN2C=C(C=C(C2=N1)C(F)(F)F)Br

Description

Ethyl 6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate features a sterically hindered trifluoromethyl group and brominated imidazopyridine core, enabling direct functionalization in cross-coupling reactions. This bench-stable building block integrates seamlessly into pharmaceutical scaffolds requiring electron-deficient heterocyclic motifs.

Application

Ethyl 6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate serves as a versatile building block for constructing imidazo[1,2-a]pyridine-based scaffolds in medicinal chemistry. The bromine at C6 enables palladium-catalyzed cross-coupling reactions, while the trifluoromethyl group enhances metabolic stability and lipophilicity. The ester functionality offers handle for derivatization, and the molecule exhibits good bench stability and compatibility with standard synthetic protocols.

Synthesis

  • Route1
    • In-stock
      5-Bromo-3-(trifluoromethyl)pyridin-2-amine|CS-W003744
      79456-34-1
    • null|null
      70-23-5
    • ~86%
    • In-stock
      Ethyl 6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate|CS-0101666
      1121051-30-6

    References

    • GLAXOSMITHKLINE LLC; BANKA, Anna; BASKARAN, Subramanian; CATALANO, John; CHONG, Pek; DICKSON, Hamilton; FANG, Jing; MAUNG, Jack; NEITZEL, Martin, Leon; PEAT, Andy; PRICE, Daniel; RAI, Roopa; ROBERTS, Christopher, Don; SHOTWELL, Brad; TAI, Vincent; ZHANG, Huichang Patent: WO2010/91411 A1, 2010 ; Location in patent: Page/Page column 79 ; WO 2010/091411 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-H320-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.6
  • LogP   3.2923
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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