(S)-3-(5-bromo-2-(2-(1-methoxyethyl)pyridin-3-yl)-1-(2,2,2-trifluoroethyl)-1H-indol-3-yl)-2,2-dimethylpropan-1-ol
[CAS# 2865162-15-6]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives
• Name: (S)-3-(5-bromo-2-(2-(1-methoxyethyl)pyridin-3-yl)-1-(2,2,2-trifluoroethyl)-1H-indol-3-yl)-2,2-dimethylpropan-1-ol
• Molecular Formula: C₂₃H₂₆BrF₃N₂O₂
• Molecular Weight: 499.36
• CAS Registry Number: 2865162-15-6
• SMILES: C1=C(C=CC3=C1C(=C(C2=C([C@H](C)OC)N=CC=C2)[N]3CC(F)(F)F)CC(C)(C)CO)Br

Discovory and Applicatios

(S)-3-(5-bromo-2-(2-(1-methoxyethyl)pyridin-3-yl)-1-(2,2,2-trifluoroethyl)-1H-indol-3-yl)-2,2-dimethylpropan-1-ol is a chiral, multifunctional intermediate used in medicinal chemistry for the construction of complex drug-like molecules. The compound features a 1H-indole core substituted at the 1-position with a 2,2,2-trifluoroethyl group, at the 3-position with a 2,2-dimethylpropan-1-ol side chain, and at the 2-position with a 2-(1-methoxyethyl)pyridin-3-yl group. The pyridine moiety is further substituted at the 5-position with a bromine atom, providing a reactive site for selective cross-coupling reactions. The stereocenter at the 3-position of the indole ensures defined three-dimensional orientation in downstream synthetic elaboration.

The bromine atom on the pyridine ring enables palladium-catalyzed reactions such as Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira couplings, allowing introduction of aryl or heteroaryl fragments. The methoxyethyl group provides a stereodefined handle, maintaining the chiral integrity of the molecule during further transformations. The trifluoroethyl substituent on the indole nitrogen can influence lipophilicity and metabolic stability of derived compounds, and the 2,2-dimethylpropan-1-ol side chain can serve as a site for further derivatization, including oxidation, esterification, or ether formation.

This intermediate is typically employed in multi-step medicinal chemistry programs where control of stereochemistry, functional group compatibility, and modularity are critical. It is particularly useful in the development of kinase inhibitors, CNS-active compounds, and other heteroaryl-containing pharmacophores. Proper handling includes storage under inert atmosphere and protection from moisture to prevent degradation or racemization, with analytical confirmation of stereochemistry and purity typically performed using chiral HPLC, NMR, and mass spectrometry.