Piperazine → 8-Piperazin-1-yl-[1,6]-naphthyridine

Participants

Reaction Conditions

Reaction Steps

To an oven-dried 100 mL flask under a nitrogen atmosphere was added 8-bromo-[1,6]-naphthyridine (1.3 g, 6.2 mmol), piperazine (3.21 g, 37.3 mmol), and sodium t-butoxide (900 mg, 9.33 mmol). The solids were suspended in anhydrous o-xylenes (40 mL), and Pd(dba) (285 mg, 5 mol %) and P(t-Bu)3 (0.31 mL, 1.24 mmol) were added. The reaction mixture was heated at 120° C. for 3 hours. The cooled reaction mixture was poured into H2O (100 mL) and extracted into EtOAc (1×100 mL) and CH2Cl2 (2×100 mL). The organic fractions were combined, dried over Na2SO4, concentrated, and the resulting oil was chromatographed (10% MeOH/CH2CH2+NH4OH) affording 470 mg (35%) of the title compound as a dark gold oil. An analytical sample was prepared as the HCl salt from EtOAc giving a brown solid: mp decomposes above 200° C. MS(+)APCI m/z 215 [M+H]+.

Provenance & Evidence