Sodium Carbonate → HCID 18507798, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-7-methyl-1-naphthalen-2-ylmethyl-3,3-bis-pyridin-4-ylmethyl-1,3-dihydro-indol-2-one (200 mg, 0.365 mmol) in 4 ml of toluene and 2.5 ml of EtOH was added tetrakis(triphenylphosphine)palladium (17 mg, 0.015 mmol) under an atmosphere of dry N2, followed by the addition of a solution of aqueous sodium carbonate (Na2CO3) (77 mg, 0.738 mmol) dissolved in 2 ml of water and 4-cyanobenzene boronic acid (101 mg, 0.686 mmol). The reaction mixture was heated to 100° C. and stirred at this temperature overnight. The reaction mixture was concentrated under vacuum and then partitioned between DCM and saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to give the crude product. It was chromatographed on silica gel eluting MeOH/NH4OH/CHCl3/(3/0.3/97) to give the titled compound of Example 10 (194 mg, 93% yield).

Provenance & Evidence