Triethylamine → Tetrabutylammonium Fluoride

Participants

Reaction Conditions

Reaction Steps

Triethyl amine (0.030 ml, 0.213 mmol), 4-bromo-2-methylpyridine (19 mg, 0.111 mmol), bis(triphenylphosphino)palladium dichloride (6 mg, 8.55 μmol), and DMF (2 ml) were added to the 25-mL flask containing the crude 3-(4-Ethynyl-1,2,3-triazol-1-yl)-1-(2,2,2-trifluoro-ethyl)-1,3,4,5-tetrahydro-1-benzazepin-2-one and the resulting brownish solution was degassed for 15 minutes by bubbling nitrogen through. Copper(I) iodide (1 mg, 5.25 μmol) was added and the mixture heated to 90° C. for 14 h. After cooling to room temperature the reaction mixture was passed through a silica gel pipette and the residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.1% TFA, to give the product as a colorless solid with some TBAF contamination. The residue was purified by column chromatography on silica gel (10 g prepacked) eluting with EtOAc/MeOH to give 3-[4-(2-Methyl-pyridin-4-ylethynyl)-1,2,3-triazol-1-yl]-1-(2,2,2-trifluoro-ethyl)-1,3,4,5-tetrahydro-1-benzazepin-2-one (11 mg) as a colorless solid.

Provenance & Evidence