1-[(2-bromophenyl)methyl]piperidin-4-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 5 mL microwave vial equipped with a stir bar was added sodium carbonate (79 mg, 0.75 mmol). The vial was dried in an oven for 16 hours, then cooled to room temperature under nitrogen. 1-(2-Bromo-benzyl)-piperidin-4-one (100 mg, 0.37 mmol), 4-fluorophenyl boronic acid (52.2 mg, 0.37 mmol) and Pd(PPh3)4 (43 mg, 0.037 mmol) were added, followed by dioxane (5 mL) water (1 mL). The resulting mixture was degassed thoroughly with nitrogen and then heated in a microwave to 100° C. for 10 minutes. The reaction was filtered and the filtrate was concentrated. The crude residue was purified via flash chromatography (heptanes/EtOAc gradient) to afford the desired product as a yellow solid (58 mg, 40% yield). MS (ESI) ink (M+H+): 283.3. To a 5 mL microwave vial equipped with a stir bar The vial was dried in an oven for 16 hours The resulting mixture was degassed thoroughly with nitrogen heated in a microwave to 100° C. for 10 minutes The reaction was filtered the filtrate was concentrated The crude residue was purified via flash chromatography (heptanes/EtOAc gradient)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 5 mL microwave vial equipped with a stir bar was added sodium carbonate (79 mg, 0.75 mmol). The vial was dried in an oven for 16 hours, then cooled to room temperature under nitrogen. 1-(2-Bromo-benzyl)-piperidin-4-one (100 mg, 0.37 mmol), 4-fluorophenyl boronic acid (52.2 mg, 0.37 mmol) and Pd(PPh3)4 (43 mg, 0.037 mmol) were added, followed by dioxane (5 mL) water (1 mL). The resulting mixture was degassed thoroughly with nitrogen and then heated in a microwave to 100° C. for 10 minutes. The reaction was filtered and the filtrate was concentrated. The crude residue was purified via flash chromatography (heptanes/EtOAc gradient) to afford the desired product as a yellow solid (58 mg, 40% yield). MS (ESI) ink (M+H+): 283.3. To a 5 mL microwave vial equipped with a stir bar The vial was dried in an oven for 16 hours The resulting mixture was degassed thoroughly with nitrogen heated in a microwave to 100° C. for 10 minutes The reaction was filtered the filtrate was concentrated The crude residue was purified via flash chromatography (heptanes/EtOAc gradient)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the procedure described for Intermediate 31, alkylation of 4-piperidone hydrochloride (1.0 g, 4.0 mmol) with 1-bromo-2-bromomethylbenzene (543 mg, 4.0 mmol) afforded the title compound (882 mg, 82% yield). HR-MS (m/z, MH+): measured 268.15

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the procedure described for Intermediate 31, alkylation of 4-piperidone hydrochloride (1.0 g, 4.0 mmol) with 1-bromo-2-bromomethylbenzene (543 mg, 4.0 mmol) afforded the title compound (882 mg, 82% yield). HR-MS (m/z, MH+): measured 268.15