Triethylamine → HCID 89610367, compound

Participants

Reaction Steps

To a stirred solution of 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxamide (13) [prepared using the same procedure as Example A step (ii) using ammonium chloride] (267 mg, 0.57 mmol) and triethylamine (710 μL, 5.10 mmol) in DCM (8 mL) at 0° C. was added trifluoroacetic anhydride (240 μL, 1.70 mmol) and the reaction allowed to warm to RT over 30 min. The reaction mixture was partitioned between DCM (50 mL) and 1 M HCl (aq.) (30 mL), the organic was washed with 1 M HCl (aq.) (20 mL), sat. NaHCO3 (aq.) (30 mL), and brine (20 mL), dried (MgSO4), filtered and volatiles removed in vacuo to afford a yellow solid. The crude residue was purified by silica gel chromatography (40 g, 0-50% EtOAc in isohexane) to afford 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarbonitrile (14) (240 mg, 97%) as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) δ: 7.47-7.27 (m, 10H), 7.30-7.20 (m, 2H), 7.05-6.91 (m, 2H), 5.26 (s, 4H), 3.79 (s, 3H).

Provenance & Evidence