Sodium Carbonate → HCID 131734227, compound

Participants

Reaction Steps

4-(Azetidin-1-yl)-5-(5-bromo-1-methyl-1H-pyrazol-4-yl)imidazo[5,1-f][1,2,4]triazine (15 mg, 0.045 mmol), [4-(trifluoromethyl)phenyl]boronic acid (9.50 mg, 0.0500 mmol), tetrakis(triphenylphosphine)palladium(0) (4.6 mg, 0.0040 mmol) and sodium carbonate (9.5 mg, 0.090 mmol) were combined in ethanol (4 mL), and the reaction mixture was heated at reflux for 18 hours. After filtration, the filtrate was concentrated in vacuo and purified via reversed-phase HPLC (Column: Waters Sunfire C18, 19×100 mm, 5 μm; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in acetonitrile (v/v); Gradient: 5% to 100% B). Yield: 4.5 mg, 0.011 mmol, 24%. Retention time: 2.32 minutes (Column: Waters Atlantis dC18, 4.6×50 mm, 5 μm; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in acetonitrile (v/v); Gradient: linear, 5% to 95% B over 4.0 minutes; Flow rate: 2 mL/minute). LCMS m/z 400.2 (M+1).

Provenance & Evidence