Benzimidazole → HCID 60673465, compound

Temperature

45 °C

A suspension of 1H-benzoimidazole (317 mg, 2.68 mmol) and potassium carbonate (495 mg, 3.58 mmol) in DMF (10 mL) was stirred at 45° C. for 1 h. To the heated suspension was added 2-Bromo-4-bromomethyl-1-methoxy-benzene (500 mg, 1.79 mmol) and the reaction was stirred at 45° C. for 4 h, cooled to room temperature and stirred at room temperature overnight. About half of the solvent was removed under vacuum, and ethyl acetate (30 mL) was added. The organic solution was washed with saturated aqueous ammonium chloride (3×30 mL), water (2×15 mL), and brine (15 mL). The organic extract was dried over anhydrous sodium sulfate and the solvent removed under vacuum to give crude product as an orange oil. The product was purified by flash silica gel column chromatography eluting with 5% methanol in dichloromethane to give the title compound (282.5 mg; 48% yield) and a second crop of 50% pure 2-Bromo-4-bromomethyl-1-methoxy-benzene (207.1 mg).

1. stirringthe reaction was stirred at 45° C. for 4 h
2. temperaturecooled to room temperature
3. stirringstirred at room temperature overnight
4. customAbout half of the solvent was removed under vacuum, and ethyl acetate (30 mL)
5. additionwas added
6. washThe organic solution was washed with saturated aqueous ammonium chloride (3×30 mL), water (2×15 mL), and brine (15 mL)
7. extractionThe organic extract
8. dry with materialwas dried over anhydrous sodium sulfate
9. customthe solvent removed under vacuum
10. customto give crude product as an orange oil
11. customThe product was purified by flash silica gel column chromatography
12. washeluting with 5% methanol in dichloromethane

ORD record

ord-5e6682d488174360b87883fc45917165

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791267B2