反应详情

To a solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (300 mg, 0.84 mmol) in CH2Cl2 (10 mL) and NEt3 (0.4 mL) was added bis(triphenylphosphine)palladium (II) chloride (20 mg, 0.028 mmol), copper (1) iodide (2 mg) and 1-octyne (0.25 mL. 1.7 mmol). The reaction mixture was stirred and refluxed under N2 atmosphere for two days and then cooled to room temperature. After washing with aqueous 10% NaOH (1X), the organic layer was dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc, 10: 1 to 10:2) to afford an oil (255 mg, 79%): 1H NMR (CDCl3, 300 MHz) δ0.88 (t, 3H, J=2.5 Hz), 1.20-1.38 (m, 4H), 1.42 (d, 4H, J=2.5 Hz), 1.44 (s, 9H), 1.90 (m, 1H), 2.00 (m, 1H), 2.40 (t, 2H, J=7.0 Hz), 3.12 (q, 4H, J=7.5 Hz), 3.32-3.44 (m, 2H), 3.90 (br, 1H), 4.08-4.20 (m, 2H), 7.10 (s, 1H), 8.08-8.30 (m, 2H); MS (CI/NH3) m/z 387 (M+H)+.

1. temperaturerefluxed under N2 atmosphere for two days
2. washAfter washing with aqueous 10% NaOH (1X)
3. dry with materialthe organic layer was dried (MgSO4)
4. concentrationconcentrated
5. customchromatographed (silica gel; hexane/EtOAc, 10: 1 to 10:2)