3-Bromobenzonitrile → HCID 67517884, compound

Participants

Reaction Conditions

Reaction Steps

To a toluene (140 mL) suspension of tris(dibenzylideneacetone)dipalladium (2.06 g, 2.25 mmol), 2-(di-tert-butylphosphino)biphenyl (0.839 g, 2.81 mmol), sodium tert-butoxide (4.05 g, 42.2 mmol) was added 3-bromobenzonitrile (5.11 g, 28.1 mmol), followed by 4-hydroxypiperidine (2.84 g, 28.1 mmol). The reaction mixture was heated to 80° C. for 5 hours while stirring under nitrogen. It was allowed to cool to room temperature, filtered, and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound. 1H NMR (500 MHz, CDCl3) δ 7.33-7.24 (m, 1H), 7.15-7.10 (m, 2H), 7.06 (d, J=7.5 Hz, 1H), 3.95-3.87 (m, 1H), 3.57 (dt, J=12.7, 4.8 Hz, 2H), 3.00 (ddd, J=12.8, 9.5, 3.2 Hz, 2H), 2.05-1.95 (m, 2H), 1.73-1.59 (m, 2H); LC-MS: m/z 203.2 (M+H).

Provenance & Evidence