Potassium Carbonate → HCID 25114689, compound

Participants

Reaction Steps

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+].

Provenance & Evidence