1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → N,N-di(1,1-dimethylethoxycarbonyl)-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-ethynylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

N,N-Di(1,1-dimethylethoxycarbonyl)-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-(2-(trimethylsilyl)ethynyl)pyridin-2-amine (713 mg, 1.2 mmol) was dissolved in methylene chloride (10 mL) and cooled to 0° C. To this was added tetrabutylammonium fluoride hydrate (163 mg, 625 μmol) in methylene chloride (1 mL). The reaction was loaded directly onto silica and chromatographed (10% ethyl acetate/hexane to 50% ethyl acetate/hexane) to give N,N-di(1,1-dimethylethoxycarbonyl)-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-ethynylpyridin-2-amine (496 mg, 1.0 mmol, 83%) as a yellow solid; 1H NMR (CDCl3): 1.37 (s, 18H), 3.35 (s, 1H), 7.30 (m, 1H), 7.40 (m, 2H), 7.89 (s, 1H), 8.75 (s, 1H).

Provenance & Evidence