Sodium hydride → 2-Chloro-1-[[2-(trimethylsilanyl)ethoxy]methyl]-benzimidazole

To a 25 mL vial which contained a suspension of NaH (140 mg, 60% in mineral oil, 3.5 mmol) in anhydrous DMF (10 mL) was added 2-chloro-1H-benzoimidazole (460 mg, 3 mmol) at 0° C. The reaction mixture which resulted was allowed to warm to rt and stir at rt for 30 min then was cooled to 0° C. and (2-Chloromethoxy-ethyl)trimethyl-silane was added to this mixture at 0° C. After warming to rt, the mixture was allowed to stir at rt for 16 h. and then was poured onto 100 mL ice-water solution. This solution was extracted with EtOAc (3×30 mL). The combined organic layers were washed with water (2×30 mL) and brine (20 mL). and dried over anhy. Na2SO4. The solvent was removed in vacuo to obtain the crude product, which was purified by silica gel flash chromatography to afford the title product (660 mg, 80%); 1H NMR (400 MHz, CDCl3); δ 0.03 (s, 9H), 0.89-0.97 (m, 2H), 3.56-3.64 (m, 2H), 5.57 (s, 2H), 7.26-7.35 (m, 2H), 7.45-7.48 (m, 1H), 7.69-7.72 (m, 1H).

1. customThe reaction mixture which resulted
2. temperaturethen was cooled to 0° C.
3. temperatureAfter warming to rt
4. stirringto stir at rt for 16 h.
5. extractionThis solution was extracted with EtOAc (3×30 mL)
6. washThe combined organic layers were washed with water (2×30 mL) and brine (20 mL)
7. customand dried over anhy
8. customThe solvent was removed in vacuo
9. customto obtain the crude product, which
10. customwas purified by silica gel flash chromatography

ORD record

ord-79c057a29ad2430096750e65be253e85

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598359B2