1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(4-fluorophenyl)-1-{2-oxo-2-[5-(trifluoromethyl)-1,3-dihydro-2H-isoindol-2-yl]ethyl}pyrrolidin-2-one

Participants

Reaction Steps

To a suspension of 2-(3-(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (0.102 g, 0.430 mmol; Example 216A) and 5-(trifluoromethyl)isoindoline hydrobromide (0.127 g, 0.473 mmol) in dichloromethane (0.75 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.114 mL, 0.645 mmol) and the reaction was stirred at room temperature. After stirring for 18 hours, the reaction was loaded onto a GraceResolv™ 4 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate/hexanes (Flow=20 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.58 (dd, J=8.5, 12.6, 2H), 7.42 (dd, J=8.1, 15.3, 1H), 7.36-7.21 (m, 2H), 7.12-6.93 (m, 2H), 4.91 (d, J=17.7, 4H), 4.29 (d, J=16.1, 1H), 4.17 (d, J=16.2, 1H), 3.85-3.54 (m, 3H), 2.72-2.50 (m, 1H), 2.19 (ddd, J=8.5, 12.9, 16.3, 1H); MS (ESI+) m/z 407.0 (M+H)+.

Provenance & Evidence