Sodium Carbonate → 4-(5-Phenyl-pyridin-3-yl)-1,4-diaza-bicyclo[3.2.1]octane dihydrochloride

Participants

Reaction Steps

4-(5-Bromo-pyridin-3-yl)-1,4-diaza-bicyclo[3.2.1]octane dihydrochoride (50 mg, 0.15 mmol) was added to a mixture of phenylboronic acid (25 mg, 0.20 mmol), tetrakis(triphenylphosphine)palladium(0) (7 mg, 0.006 mmol), sodium carbonate (63 mg, 0.60 mmol) in EtOH (5 mL) and water (5 mL). The reaction mixture was placed in an oil bath at 80° C. for 3 h, and then 60° C. for 18 h. The mixture was cooled to RT, diluted with water (10 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was dissolved in EtOH (10 mL) and conc. HCl (0.2 mL) was added. The mixture was concentrated and EtOH (10 mL) was added and the solution was concentrated. This procedure was repeated three times and the resulting solid was triturated in EtOAc. The remaining solids were collected via filtration to give 40 mg (78%) of the title compound: (data for free base) 1H NMR (CD3OD, 400 MHz) δ 8.55 (br s, 1H), 8.50 (br s, 1H), 8.33 (br s, 1H), 7.83-7.81 (m, 2H), 7.60-7.53 (m, 3H), 5.12 (br s, 1H), 4.06-4.04 (m, 1H), 3.70-3.59 (m, 5H), 3.54-3.51 (m, 2H), 2.51-2.47 (m, 1H), 2.26-2.23 (m, 1H); APCI MS m/z 266.2 (M+1).

Provenance & Evidence