Pyrrolidine → 3-Bromo-5-(pyrrolidin-1-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dibromopyridine (5.5 g, 23.22 mmol) in toluene (100 mL) was added BINAP (0.840 g, 1.350 mmol), Pd2(dba)3 (0.412 g, 0.45 mmol), sodium tert-butoxide (6.49 g, 67.5 mmol) and pyrrolidine (1.86 mL, 22.50 mmol). The reaction mixture was degassed (N2, 10 min) and then heated at 100° C. for 2 h. The reaction mixture was cooled to RT and filtered through celite. The filtrate was evaporated and the residue purified by silica gel chromatography, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, to afford the title compound (3.88 g). LCMS (A) m/z: 227/229 [M+1]+, Rt 0.87 min (acidic),

Provenance & Evidence