1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (E)-7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[isoindoline-1,4'-piperidin]-3-one

Participants

Reaction Steps

A mixture of 7-bromospiro[isoindoline-1,4′-piperidin]-3-one (194 mg, 0.69 mmol), 3-(2-(trifluoromethyl)phenyl)acrylic acid (100 mg, 0.46 mmol), EDCI (181 mg, 0.92 mmol), HOBt (124 mg, 0.92 mmol) and i-Pr2NEt (1 mL) was stirred at rt overnight. The mixture was washed with 5% aq HCl, and the organic layer was concentrated to give a residue which was purified by preparative HPLC to afford (E)-7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[isoindoline-1,4′-piperidin]-3-one (5 mg, 2%). 1H NMR (400 MHz, CDCl3): δ=1.53 (m, 2H), 2.98 (m, 3H), 3.42 (m, 1H), 4.23 (m, 1H), 4.50 (m, 1H), 4.93 (m, 1H), 6.80 (m, 1H), 7.33 (m, 1H), 7.40 (m, 1H), 7.50 (m, 1H), 7.65 (m, 3H), 7.77 (m, 1H), 7.95 (m, 1H), 8.50 (m, 1H).

Provenance & Evidence