tert-Butyl piperazine-1-carboxylate → tert-butyl 4-(1H-indol-6-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (30 mg, 0.026 mmol), tert-butyl piperazine-1-carboxylate (570 mg, 3.06 mmol), X-Phos (CAS Number: 564483-18-7, 40 mg, 0.077 mmol) and 6-bromo-1H-indole (500 mg, 2.55 mmol) were added to THF (2 mL) in a sealed reactor. After adding lithium hexamethyldisilazide (LHMDS; 1 M in THF, 5.61 mL, 5.6 mmol) at room temperature, the mixture solution was stirred at 65° C. for 24 hours in a sealed state. After cooling to room temperature, the reaction was terminated with saturated ammonium chloride aqueous solution. After extraction with ethyl acetate, the collected organic layer was washed with saturated sodium bicarbonate aqueous solution and brine and then concentrated by drying with anhydrous sodium sulfate. The residue was purified by chromatography (silica gel, EA:Hx=1:2). The target compound (334 mg) was obtained as white solid.

Provenance & Evidence