Ammonium Chloride → 3-{1-[6-(2,4-Difluorophenyl)pyridin-2-yl]-2-oxobut-3-yn-1-yl}-4-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[1-[6-(2,4-difluorophenyl)pyridin-2-yl]-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-fluorobenzonitrile (from Step D above, 40 g, 89.0 mmol) in THF (750 mL) was added TBAF (133 mL, 133.6 mmol) at 0° C. After stirring at 0° C. for 15 min, the reaction was poured into aqueous NH4Cl, and extracted with EtOAc (2×). The organic layers were combined, washed with H2O, brine, dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexanes/methylene chloride) to give title compound (24 g). 1H NMR (CDCl3) δ: 7.80 (q, 1H), 7.72 (m, 3H), 7.51 (d, 1H), 7.31 (t, 1H), 7.04 (m, 1H), 6.97 (m, 1H), 6.60 (d, 1H), 3.14 (s, 10H).

Provenance & Evidence