Sodium Carbonate → HCID 59323812, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (RS)-4-(4-bromo-phenyl)-4,5-dihydro-oxazol-2-ylamine (80 mg; example 20) at r.t. in 1,2-dimethoxyethane (4 ml) under an argon atmosphere were added PdCl2(dppf) (24 mg), 10% aq. Na2CO3 (1 ml) and 4-fluorophenylboronic acid (186 mg). The mixture was heated to 85° C. and stirring at that temperature was continued for 18 h. The dark brown mixture was cooled to r.t., diluted with EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc. The combined organics were washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (RS)-4-(4′-fluoro-biphenyl-4-yl)-4,5-dihydro-oxazol-2-ylamine (46 mg) as off-white solid. MS (ISP): 257.0 ([M+H]+)

Provenance & Evidence