反应详情

A mixture of (5-bromopyridin-2-yl)methanol (0.205 g, 1.09 mmol), (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine (0.13 M in isopropanol, 8.4 mL, 1.09 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (0.045 g, 0.05 mmol), and 2 M potassium carbonate (1.64 mL, 3.28 mmol) was irradiated in a microwave synthesizer at 140° C. for 20 min. The solution was filtered through a pad of celite and concentrated in vacuo. The residue was purified by column chromatography using a gradient of ethyl acetate in heptane. The crude was dissolved in chloroform and insoluble material was removed. The solvent was evaporated in vacuo yielding an oil, 0.360 g (76%); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.46 (d, 1 H), 7.79 (dd, 1 H), 7.54 (d, 1 H), 7.24-7.34 (m, 8 H), 7.06-7.22 (m, 3 H), 6.69-6.83 (m, 2 H), 5.51 (t, 1 H), 4.64 (d, 2 H), 4.28-4.39 (m, 1 H), 3.99-4.10 (m, 1 H), 3.59-3.74 (m, 4 H), 2.86-3.11 (m, 1 H), 2.39-2.49 (m, 1 H); MS (APPI/APCI) m/z 437[M+H+].

1. customwas irradiated in a microwave synthesizer at 140° C. for 20 min
2. filtrationThe solution was filtered through a pad of celite
3. concentrationconcentrated in vacuo
4. customThe residue was purified by column chromatography
5. dissolutionThe crude was dissolved in chloroform
6. custominsoluble material was removed
7. customThe solvent was evaporated in vacuo
8. customyielding an oil, 0.360 g (76%)