Sodium Carbonate → 10-(4-benzyloxy-phenyl)-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene

Participants

Reaction Conditions

Reaction Steps

To a solution of 10-chloro-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (221 mg, 1.0 mmol) in toluene (4 mL) was added 4-benzyloxyphenyl boronic acid (100 mg, 2.0 mmol), tetrakis(triphenylphosphine) palladium (5.7 mg, 0.0047 mmol), and 2M aq Na2CO3 (1.0 mL, 2.0 mmol). The reaction was flushed with argon and stirred at 80° C. overnight. The solution was cooled, followed by dilution with EtOAc (3 mL). The organic layer was washed with H2O, brine, dried over MgSO4, and concentrated. The residue was purified via flash chromatography (5-30% EtOAc/Hexane) to provide 10-(4-benzyloxy-phenyl)-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (200 mg, 54% yield).

Provenance & Evidence