Water → HCID 66779661, compound

Participants

Reaction Steps

To a 20-mL glass vial was added 3-[2-(3,4-dimethoxyphenyl)furo[3,2-b]pyridin-7-yl]-2-methylaniline (19.20 mg; 0.05 mmol), triethylamine (0.01 ml; 0.11 mmol) suspended in DCM (2.00 ml). 3-(trifluoromethyl)benzoyl chloride (16.67 mg; 0.08 mmol) was then added. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture which was then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude mixture was purified using Biotage column chromatography (20-100% EtOAc/Hexanes). Fractions containing the desired product were combined and concentrated. The mixture was then purified using preparative HPLC to afford the title compound as a yellow solid (3.80 mg, 13%). HPLC (method F): 100%, RT=4.531 min. 1H NMR (CDCl3) δ [ppm] 8.58 (d, 1H), 8.19 (s, 1H), 8.12 (d, 1H), 7.96 (d, 1H), 7.88-7.84 (m, 2H), 7.71-7.68 (m, 2H), 7.60-7.47 (m, 3H), 7.39-7.38 (m, 2H), 7.00-6.97 (m, 1H), 4.01 (s, 3H), 3.96 (s, 3H), 2.27 (s, 3H). MS: m/z=533 [M+H]+, RT=3.91 min.

Provenance & Evidence