Sodium Carbonate → HCID 70177971, compound

Participants

Reaction Steps

A mixture of 0.44 g (1 mmol) of 2-bromo-6-chloro-1-(2,3-di-O-acetyl-5-deoxy-β-D-ribofuranosyl)-1H-benzimidazole and 0.17 g (1.6 mmol) of sodium carbonate in 8 mL of MeOH, 8 mL of EtOH and 2 mL of water was stirred at room temperature for 6 h. The reaction mixture was concentrated and redissolved in 50 mL of EtOAc. After 2 washings with saturated brine, the EtOAc solution was dried over MgSO4. Solvent removal resulted in a crude product which was flash column chromatographed on silica gel with EtOAc/hexane (1:1) to give 0.24 g (69%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ1.4 (d, 3H, CH3), 3.8-3.9 (m, 1H, CH), 3.9-4 (m, 1H, CH), 4.45 (q, 1H, CH), 5.21 (d 1H, OH), 5.45 (d, 1H, OH), 5.8 (d, 1H, CH), 7.3 (d, 1H, aromatic), 7.6 (s,1H, aromatic), 7.62 (d, 1H, aromatic).

Provenance & Evidence