Trimethylsilyl triflate → HCID 53700596, compound

Temperature

65 °C

To a suspension of 4-bromo-2,5,6-trichloro-1H-benzimidazole (0.30 g, 1 mmol), in acetonitrile (5 mL) was added N,O-bis(trimethylsilyl)acetamide (0.25 mL, 1 mmol). The resulting mixture was allowed to stir at 65° C. for 15 min., followed by the addition of 1,2,3-tri-O-acetyl-5-deoxyribofuranose (0.31 g, 1.2 mmol) in acetonitrile (5 mL) and trimethylsilyltrifluoromethane sulfonate (0.25 mL, 1.3 mmol). The mixture was allowed to stir at 65° C. for 20 min and was then allowed to cool to RT. The mixture was diluted with ethyl acetate and was washed with a saturated NaHCO3/NaCl solution, dried over MgSO4 and the solvents were removed by rotary evaporation. The product was purified by flash chromatography using chloroform as eluent followed by recrystallization from methanol to provide 0.28 g (55%) of the title compound as white crystals; m.p. 138-141° C.; 1H NMR (DMSO-d6) δ: 8.18 (s, 1H), 6.19 (d, 1H), 5.61 (dd, 1H), 5.25 (dd, 1H), 4.24 (m, 1H), 2.14 (s, 3H), 2.02 (s, 3H), 1.50 (d, 3H).

1. stirringto stir at 65° C. for 20 min
2. temperatureto cool to RT
3. washwas washed with a saturated NaHCO3/NaCl solution
4. dry with materialdried over MgSO4
5. customthe solvents were removed by rotary evaporation
6. customThe product was purified by flash chromatography
7. customfollowed by recrystallization from methanol

ORD record

ord-62129636baaf43248e9cfa8bf5b031cc

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06413938B1