Sodium Carbonate → HCID 24800422, compound

Participants

Reaction Conditions

Reaction Steps

0.12 g (0.316 mmol) (7-bromo-benzooxazol-2-yl)-(3,4,5-trimethoxy-phenyl)-amine and 0.048 g (0.353 mmol) 3-tolyl boronic acid are dissolved in 4 ml 1,2-dimethoxy-ethane, a solution of 0.1 g (0.95 mmol) Na2CO3 (in 0.5 ml water) is added and a stream of argon is bubbled through the mixture in order to exclude oxygen from the reaction mixture. Tetrakis (triphenylphosphine) palladium (76 mg, 0.064 mmol) is added and the reaction mixture is stirred at 100° C. or 3 h. After that the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane:EtOAc=3:1=>1:1) to afford the title compound as an off-white solid, m.p. 153-155° C. Rt=2.54 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min). MS: 391 (M+1)+; m.p. 155-158° C.

Provenance & Evidence