Sodium Carbonate → 2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A suspension of Intermediate 66.3 (100 mg, 0.13 mmol), 2-formyl phenylboronic acid (30 mg, 0.2 mmol), Na2CO3 (56 mg, 0.52 mmol) in 3:1 DME/H2O (4 mL) was degassed and then added in Pd(PPh3)4 (10 mg). The reaction mixture was heated to 150° C. for 8 min in microwave. The reaction mixture was then partionated between EtOAc and sat. NaCl, the organic layer was collected and dried over (Na2SO4), filtered and concentrated. The residue was subject to chromatographic purification (0-30% EtOAc/hexanes gradient), 100 mg (65%) of Intermediate 122.1 was obtained. LCMS (2 min gradient) RT 2.35 min, 798.3 (M+H).

Provenance & Evidence