Ethyl Acetate → HCID 86656481, compound

Participants

Reaction Steps

Solid Pd(PPh3)4 (7.66 mg, 6.63 μmol) was added to a stirred, cloudy solution of 14 (174 mg, 0.17 mmol), Na2CO3 (28 mg, 0.22 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)aniline (47 mg, 0.22 mmol) in toluene (2-5 mL), EtOH (1.25 mL) and H2O (125 mL) at room temperature. The reaction mixture was allowed to stir under a N2 atmosphere for 24 hours at which point the reaction was deemed complete by LC/MS major peak (@ 3.97 min, FW=1016, M+Na) and TLC (EtOAc). The solvent was removed by evaporation in vacuo and the resulting residue partitioned between EtOAc (60 mL) and H2O (30 mL). The layers were separated and the organic phase was washed with H2O) (20 mL), brine (30 mL) dried (MgSO4) filtered and evaporated in vacuo to provide the crude product 123 mg, 75% yield.

Provenance & Evidence