Pyrrolidine → HCID 68540432, compound

Participants

Reaction Steps

To a solution of (2E)-3-(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (10) (0.135 g, 0.33 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (0.043 mL, 0.49 mmol) under N2. The resultant mixture was stirred at room temperature for 2 h. Reaction mixture was concentrated under reduced pressure to afford the crude acid chloride. The acid chloride was dried (Na2SO4) and re-dissolved in CH2Cl2 (5 mL) at room temperature. To the above solution pyrrolidine (0.055 ml, 0.66 mmol) was introduced slowly and the mixture was stirred for 12 h. Reaction mixture was concentrated under reduced pressure to afford the crude amide. The product was purified by SiO2 column chromatography using hexanes:EtOAc (9:1 to 3:2) as an eluent to afford 0.146 g (96%) of the title compound (243) as a white foam. 1H NMR (400 MHz, CDCl3): δ 7.71 (d, J=9.2 Hz, 1H), 7.55 (s, 1H), 7.54 d, J=15.6 Hz, 1H), 7.27-7.20 (m, 5H), 7.13-7.11 (m, 3H), 7.03 and 7.01 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.57 (d, J=8.8 Hz, 2H), 6.51 (d, J=15.2 Hz, 1H), 3.91 (s, 3H), 3.55 (t, J=6.8 Hz, 4H), 2.22 (s, 3H), 1.94 (quintet, J=6.4 Hz, 2H), 1.85 (quintet, J=6.8 Hz, 2H), 2.26 (s, 3H). LCMS (ESI) m/z 464.15 (M+H)+.

Provenance & Evidence