2,6-Lutidine → HCID 69425288, compound

Participants

Reaction Steps

Phenylboronic acid (0.12 g, 1.0 mmol), Cu(OAc)2 (0.036 g, 0.2 mmol), and myristic acid (0.046 g, 0.2 mmol) were combined in a 100-mL round-bottom flask with a large stir bar. A rubber septum was attached, and dry toluene (2 mL), 2,6-lutidine (0.116 mL, 1.0 mmol), and {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate (0.045 g, 0.09 mmol) were successively added. The resulting mixture was stirred at a high rate for 24 h, diluted with ethyl acetate (10 mL), filtered through a plug of silica gel, and then purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a yellow solid (0.05 g, 94%). MS (ESI) m/z 469; MS (ESI) m/z 467; HRMS: calcd for C29H19F3N2O, 468.1449; found (ESI, [M−H]−), 467.1362; Anal. Calcd for C29H19F3N2O: C, 74.35; H, 4.09; N, 5.98. Found: C, 74.27; H, 3.72; N, 5.82.

Provenance & Evidence