2-Bromopyridine → HCID 67376913, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of BINAP (31 mg, 0.05 mmol) and Pd2dba3 (230 mg, 0.03 mmol) were taken in toluene and the solution was heated to 85° C. for 10 min under argon atmosphere. The solution was cooled to 40° C. and (1S,4S)-2-boc-2,5-diazabicyclo[2.2.1]heptane (250 mg, 1.26 mmol) was added, followed by 2-bromo pyridine (218 mg, 1.38 mmol) and sodium tert-butoxide (194 mg, 2.0 mmol). The reaction mixture was heated to 85° C. for 5 h, cooled to room temperature, diluted with EtOAc and filtered through Celite. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluent 20-30% EtOAc in petroleum ether) to get (1S,4S)-tert-butyl 5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (170 mg, yield 49%). 1H NMR (300 MHz, CDCl3) δ 8.14 (d, J=4.6 Hz, 1H), 7.47-7.42 (t, J=7.7 Hz, 1H), 6.59-6.55 (m, 1H), 6.35-6.32 (d, J=8.6 Hz, 1H), 4.90-4.79 (m, 1H), 4.67-4.52 (m, 1H), 3.57-3.35 (m, 4H), 1.96-1.92 (m, 2H), 1.46-1.42 (m, 9H). MS (ESI) m/z: Calculated for C15H21N3O2: 275.16. found: 276.1 (M+H)+

Provenance & Evidence