2-Bromopyridine → 2-(4-Boc-Aminopiperidino)pyridine

Participants

Reaction Conditions

Reaction Steps

The reaction mixture of tert-butyl piperidin-4-ylcarbamate (200 mg, 0.10 mmol), 2-bromopyridine (205 mg, 1.30 mmol), Pd2(dba)3 (18.0 mg, 0.02 mmol), Xantphos (35.0 mg, 0.06 mmol) and Cs2CO3 (490 mg, 1.50 mmol) was heated at 100° C. for 1 day. Additional 2-bromopyridine (205 mg, 1.30 mmol), Pd2(dba)3 (18.0 mg, 0.02 mmol), Xantphos (35.0 mg, 0.06 mmol), Cs2CO3 (490 mg, 1.50 mmol) were added to the reaction mixture, and heated at 100° C. for 1 day. The reaction mixture was cooled to room temperature, diluted with EtOAc and water. The separated aqueous layer was extracted with EtOAc, the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc) to give tert-butyl 1-(pyridin-2-yl)piperidin-4-ylcarbamate (86.8 mg, 31%) as a pale yellow solid. m/z=278.06 [M+1]+.

Provenance & Evidence