N-Iodosuccinimide → HCID 89610330, compound

Participants

Reaction Conditions

Reaction Steps

N-Iodosuccinimide (1.77 g, 7.57 mmol) was added to a solution of ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (27) [prepared using the same procedure as Example E step (i) using (5) as starting material] (3.0 g, 6.56 mmol) in DMF (60 mL) and stirred at 0° C. for 10 min. The mixture was partitioned between sat. Na2S2O3 (aq.) (100 mL) and Et2O (250 mL), the organic layer was separated and washed with sat. Na2S2O3 (aq.) (100 mL), brine (100 mL) dried (MgSO4), filtered and solvents removed in vacuo. The crude residue was purified by silica gel chromatography (120 g, 0-40% Et2O in isohexane) to afford ethyl 3,4-bis(benzyloxy)-5-iodo-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (28) (2.92 g, 76%) as a white solid: m/z 584 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.29 (m, 10 H), 7.14-7.05 (m, 2H), 7.03-6.92 (m, 2H), 5.12 (s, 2H), 5.00 (s, 2H), 3.97 (q, J=7.1 Hz, 2H) 3.82 (s, 3H), 0.99 (t, J=7.1 Hz, 3H).

Provenance & Evidence