Synthesis, crystal structure and DFT study of tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate

Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate has three groups: indoline, boronate and tert-butylcarbonyl, which is an important pharmaceutical intermediate. The target compound is obtained from 5-bromoindole as raw material. The compound was confirmed by H-1 NMR, C-13 NMR, MS and FT-IR. DFT is used to computationally optimize the structure of compounds. The crystallographic analysis of its structure was carried out by X-ray single crystal diffraction. The results show that the DFT-optimized structure matches the crystal structure determined by X-ray single crystal diffraction. The molecular electrostatic potential and frontier molecular orbital of the compound were studied by DFT, revealing physicochemical properties of the compound.