(Trimethylsilyl)imidazole → HCID 178437186, compound

Temperature

0 °C

Titanium tetrachloride (3.28 ml, 29.9 mmol) was added to anhydrous chloroform (25 mL) at 0° C. 1-Trimethylsilanyl-1H-imidazole (4.38 ml, 29.9 mmol) in chloroform (25 ml) was added slowly (6 to 7 m) to the TiCl4 solution. The resulting orange solid mixture was stirred at 0° C. for 30 m followed by the addition of (13) (3.53 g, 15.0 mmol) in chloroform (15 mL). The mixture was warmed to room temperature and stirred overnight. The mixture was quenched with water (60 mL). The two layers were separated and the organic layer was extracted twice with water (40 mL). The pooled aqueous layer was neutralized with 4 M NaOH to pH>8. The basic aqueous layer was to extracted with dichloromethane numerous times. The pooled organic layers were washed with brine once, and dried over magnesium sulfate. The mixture was filtered, and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane to give 8-(1-(1H-imidazol-4-yl)ethyl)quinoline (14) as an off white solid (1.61 g, 7.22 mmol, 48% yield.)

1. temperatureThe mixture was warmed to room temperature
2. stirringstirred overnight
3. customThe mixture was quenched with water (60 mL)
4. customThe two layers were separated
5. extractionthe organic layer was extracted twice with water (40 mL)
6. extractionto extracted with dichloromethane numerous times
7. washThe pooled organic layers were washed with brine once
8. dry with materialdried over magnesium sulfate
9. filtrationThe mixture was filtered
10. customthe solvent was removed under vacuum
11. customThe residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane

ORD record

ord-01304346be49459fb96567d0b05e5b9b

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119807B2