Pyridine → 2,2,2-Trifluoro-1-(1-methyl-1H-indol-3-yl)-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethanol

Participants

Reaction Steps

A mixture of 70 mg (0.20 mmol) of 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol, 65 mg (1.97 mmol) of 3-pyridyl boronic acid ester, 55 mg (0.3 mmol) of copper acetate and 50 μL (0.62 mmol) of pyridine in dry dichloromethane was stirred at room temperature. Oxygen gas was bubbled into the solution for 5 minutes and the mixture was stirred in a sealed tube. The reaction was monitored by LC-MS indicating partial conversion to product at 3 hours. The mixture was stirred overnight for 18 hours and then diluted with brine and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, and absorbed onto silica gel and first purified by Combiflash chromatography using a 0-80% EtOAc-hexanes gradient and then by preparative TLC using 20% EtOAc-hexanes. Crystallization from ether-hexanes to gave 20 mg (26%) of the title compound as a colorless powder.

Provenance & Evidence