Benzylamine → HCID 59343445, compound

Participants

Reaction Conditions

Reaction Steps

3,5-Dibromopyridine (20.0 g, 84.4 mmol) and benzylamine (9.23 mL, 84.4 mmol) were dissolved in toluene (100 mL). Pd2(dba)3 (1.55 g, 1.69 mmol), BINAP (2.10 g, 3.38 mmol) and sodium tert-butoxide (12.2 g, 127 mmol) were added to the reaction mixture. The reaction was heated to 80° C. for 16 h, then allowed to cool to ambient temperature, diluted with ether (400 mL) and washed with brine (3×100 mL). The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (25% EtOAc in hexanes) to afford the title compound as a slightly yellow solid (14.75 g, 66%). MS (DCI/NH3) m/z 263 (M+H)+.

Provenance & Evidence