Sodium Carbonate → HCID 18507797, compound

Participants

Reaction Conditions

Reaction Steps

4-(6-Bromo-2-oxo-3,3-bis-pyridin-4-ylmethyl-2,3-dihydro-indol-1-ylmethyl)-N,N-dimethyl-benzenesulfonamide (306 mg, 0.517 mmol) was dissolved in a solution of 6 ml of toluene and 1 ml of EtOH under an atmosphere of dry N2. To this solution was added tetrakis(triphenylphosphine)palladium (0) (34 mg, 0.029 mmol) followed by a solution of Na2CO3 (126 mg, 1.19 mmol) dissolved in 1 ml of water and 4-formylbezeneboronic acid (116 mg, 0.776 mmol). The reaction mixture was heated to 100° C. and reacted at this temperature overnight. The reaction mixture was cooled to ambient temperature and then partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was washed two more times with EtOAc. The combined EtOAc layers were dried over Na2SO4, filtered and concentrated under vacuum to give a dark oil. The oil was purified using radial chromatography eluting with MeOH/DCM (5:95) to give 258 mg of the titled compound as a solid.

Provenance & Evidence