Imidazole → (2-Bromoethoxy)(tert-butyl)diphenylsilane

Temperature

0 °C

Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 927 mg (corresponding to 2.76 mmol) of 2-(3′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine (FIG. 2-8, Step 2). Separately, 2.50 g (corresponding to 20.0 mmol) of 2-bromoethanol and 2.72 g (corresponding to 40.0 mmol) of imidazole were dissolved in 10 mL of dimethylformamide, and cooled to 0° C. Then, 5.50 g (corresponding to 20.0 mmol) of t-butyldiphenylchlorosilane was added thereto. After the reaction mixture was stirred at room temperature for 18 hours, a saturated sodium chloride solution was added, and extracted three times with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1) to obtain 7.04 g (corresponding to 19.4 mmol) of 1-bromo-2-(t-butyldiphenylsiloxy)ethane (FIG. 2-8, Step 3).

1. customPrecipitates
2. filtrationwere filtered
3. customrecovered from the resulting mixture
4. washsufficiently washed with water
5. customdried under reduced pressure
6. extractionextracted three times with ethyl acetate
7. dry with materialThe combined ethyl acetate layers were dried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe resulting crude product was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1)

ORD record

ord-7d35400a74ea4a56bdc6599ac695854d

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08303935B2