Benzimidazole → HCID 54186712, compound

Participants

Reaction Steps

The title compound was prepared according to General Procedure IV using 6-Chloro-5-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.37 g, 0.87 mmol), 30 ml tetrahydrofuran (Aldrich Sure Seal, Milwaukee), and a total of 1.2 g (7.0 mmol) of N-bromosuccinimide that was added in ca 0.2 equivalents/benzimidazole every 15 min over 1 h. The product from work-up by General Procedure IV was purified on a silica gel column (2.5×20 cm, 230-400 mesh) with dichloromethane containing 0.5% methanol to give 2-Bromo-6-chloro-5-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.33 g, 0.66 mmol, 75%); MS (ES+): m/z (rel. intensity) 526 (1.0, M+23 (Na)); 1H NMR (DMSO-d6) δ8.18 (s,1H), 7.62 (s, 1H), 5.97-5.904(d, 1H, J=9.4 Hz), 5.78-5.60 (m, 3H), 4.20-4.10 (m, 1H), 4.05-3.97 (m, 1H) 2.41 (s, 3H), 2.25 (s, 3H), 2.04 (s, 3H), 1.78 (s, 3H)

Provenance & Evidence