反应详情

A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (0.75 g, 3.3 mmol) in anhydrous dimethylformamide (9 ml) is treated with HATU (1.27 g, 3.3 mmol) and diisopropylethylamine (1.1 ml, 6.1 mmol). The reaction mixture is stirred 15 mins. at ambient temperature before being treated with a solution of 3-(piperidin-4-yl)-benzonitrile (0.6 g, 3 mmol) in dimethylformamide (6 ml). The reaction mixture is stirred at ambient temperature 2 hours, concentrated under vacuum and the residue partitioned between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate ((45 ml). The organic layer is dried (magnesium sulfate), concentrated under vacuum and the residue chromatographed on silica gel (dichloromethane/methanol 39:1) to give the title compound as a yellow oil (0.53 g). 1H NMR (CDCl3, 500 MHz) δ8.80 (s, 1H), 8.63 (s, 1H), 8.00 (s, 1H), 7.50 (m, 9H), 4.90 (br m, 1H), 3.85 (br m, 1H), 3.28 (m, 1H), 2.90 (m, 2H), 1.91 (m, 1H), 1.75 (m, 3H). EI MS M++H: 392.

1. stirringThe reaction mixture is stirred at ambient temperature 2 hours
2. concentrationconcentrated under vacuum
3. customthe residue partitioned between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate ((45 ml)
4. dry with materialThe organic layer is dried (magnesium sulfate)
5. concentrationconcentrated under vacuum
6. customthe residue chromatographed on silica gel (dichloromethane/methanol 39:1)