Pyridine → HCID 11486376, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 37A (69.8 mg, 0.272 mmol) and DMF (1 drop) in CH2Cl2 (2 mL) was treated with (COCl)2 (29 mL, 0.33 mmol). After stirring for 5 hours, the mixture was concentrated and the residue dissolved in CH2Cl2 (2 mL). The mixture was treated with DMAP (35.8 mg, 0.29 mmol), pyridine (22 mL, 0.27 mmol), and 4-trifluoromethylaniline (41 mL, 0.33 mmol). The mixture was heated at 60° C. for 15 hours, allowed to cool to room temperature, diluted with 1N HCl (4 mL), extracted with CH2Cl2 (2×4 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (15% ethyl acetate in hexanes) to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ 8.02 (d, 2H), 7.93 (br s, 1H), 7.80 (d, 2H), 7.77 (m, 1H), 7.68 (d, 2H), 7.66 (d, 2H), 6.88 (m, 1H); MS (m/z) 400, 417.

Provenance & Evidence