tert-Butyl piperazine-1-carboxylate → HCID 58913155, compound

Participants

Reaction Conditions

Reaction Steps

Palladium (II) acetate (37.9 mg, 0.17 mmol) and 2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (158 mg, 0.34 mmol) were dissolved in toluene (3 mL) and the resulting solution degassed and purged with nitrogen. The mixture was warmed to 50°C for 15 mins. In a separate vessel, were mixed tert-butyl piperazine-1-carboxylate (314 mg, 1.69 mmol), tert-butyl 7-bromo-1H-indole-1-carboxylate (500 mg, 1.69 mmol) and sodium-t-butoxide (243 mg, 2.53 mmol) in toluene at ambient temperature. The mixture was degassed and purged with nitrogen. The catalyst solution was added and the resulting mixture heated at 100°C under nitrogen overnight. The main product of the reaction is 7-bromoindole. Boc has been lost (high temp, base). Only small trace desired product visible in UPLC. Reaction abandoned. Try lower temps, different base?

Provenance & Evidence