Triphenylphosphine → 2,4-Dichloro-6-cyclopropylbenzylamine

Participants

Reaction Conditions

Reaction Steps

To a soln. of 2-(2-bromo-4,6-dichlorobenzyl)isoindoline-1,3-dione (1.96 mmol) in 16 mL toluene and 0.8 mL water were added K3PO4 (6.85 mmol), PPh3 (0.23 mmol), cyclopropylboronic acid (2.35 mmol) and Pd(OAc)2 (0.15 mmol). The mixture was stirred at 80° C. for 24 h when another portion of cyclopropylboronic acid (1.96 mmol) and Pd(OAc)2 (0.15 mmol) were added. The reaction mixture was stirred at 80° C. for further 4 days, cooled to RT, quenched with sat. aq. NaHCO3 solution and extracted with EtOAc. The comb. org. layers were dried over MgSO4 and conc. in vacuo to give a crude white solid. This solid was dissolved in 15 mL EtOH and 12.6 mL of hydrazine monohydrate was added. After stirring at RT for 30 min, EtOAc was added. The aq. phase was basified with 1M NaOH soln. and extracted 3 times with EtOAc. The comb. org. layers were dried over MgSO4 and conc. Purification with CC (KP-NH™ from Biotage) gives the desired compound as red/brown oil.

Provenance & Evidence