Water → HCID 67286575, compound

To a stirred suspension of 1H-benzoimidazol-4-ol (440 mg, 3.28 mmol) in THF (13 mL) at room temperature was added NaH (60% dispersion in mineral oil; 276 mg, 6.89 mmol) in 3 portions over 15 min. The mixture was stirred at room temperature for 1.5 hours before it was heated to 65° C. for 30 min. The THF was removed and replaced with DMF (10 mL) and the mixture was warmed to 65° C. for 30 min. The mixture was cooled to 10° C., 2-(trimethylsilyl)ethoxymethyl chloride (1.19 mL, 6.72 mmol) was added dropwise and the mixture was stirred at room temperature overnight. H2O and Et2O were added, the mixture was filtered and the phases separated. The aqueous phase was extracted into Et2O (×3), dried (MgSO4) and concentrated in vacuo. The product was purified by SiO2 chromatography and followed by trituration with Et2O to provide the title compound (177 mg).

1. temperaturewas heated to 65° C. for 30 min
2. customThe THF was removed
3. temperaturethe mixture was warmed to 65° C. for 30 min
4. temperatureThe mixture was cooled to 10° C.
5. stirringthe mixture was stirred at room temperature overnight
6. filtrationthe mixture was filtered
7. customthe phases separated
8. extractionThe aqueous phase was extracted into Et2O (×3)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated in vacuo
11. customThe product was purified by SiO2 chromatography

ORD record

ord-69caa8770788425e8e60e04fc4c75f69

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598217B2