Tetrabutylammonium Fluoride → 3-(1,3-Benzoxazol-2-yl)-5-ethynyl-pyridin-2-amine

Participants

Reaction Steps

Tetrabutylammonium fluoride 1.0M in THF (0.629 ml) was added to a stirred solution of 3-(1,3-benzoxazol-2-yl)-5-(2-trimethylsilylethynyl)pyridin-2-amine (0.370 g) in THF (10 ml) at room temperature. The resulting solution was stirred for 1 hour. A yellow precipitate appeared during the reaction. After concentration, the crude product was purified by flash chromatography on silica gel eluting with 0 to 15% ethyl acetate in dichloromethane to afford 3-(1,3-benzoxazol-2-yl)-5-ethynyl-pyridin-2-amine (225 mg) as a solid; NMR Spectrum: (DMSOd6) 4.20 (s, 1H), 7.42-7.51 (m, 2H), 7.80 (dd, 1H), 7.85 (dd, 1H), 8.04 (bs, 2H), 8.31 (d, 1H), 8.36 (d, 1H); Mass spectrum: M+H+: 236

Provenance & Evidence