Chlorotrimethylsilane → 2-bromo-6-(trimethylsilyl)pyridine

Temperature

0 °C

n-Butylmagnesium chloride (4.00 mmol) in 2.00M tetrahydrofuran solution (2.00 mL) was added to ice-cooled n-butyllithium (8.06 mmol) in 1.55M hexane (5.20 mL). The mixture was stirred at 0° C. for 15 minutes, and 2,6-dibromopyridine (2.37 g, 10.0 mmol) in toluene (25 mL) was added thereto below 10° C. over a period of 10 minutes or more. The resultant suspension was stirred at 0° C. for one hour, and chlorotrimethylsilane (13 mmol, 1.65 mL)) was added thereto. After the mixture was stirred at 0° C. for one hour and at room temperature for 1.5 hours, an aqueous solution (20 mL) of 1M acetic acid was added thereto. The reaction mixture was extracted twice with ethyl acetate (50 mL). The organic phase was separated, washed with water (10 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give a residue. The residue was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (20:1, v/v) to give the title compound (881 mg, about 38% yield) as colorless powder.

1. waitbelow 10° C. over a period of 10 minutes or more
2. stirringAfter the mixture was stirred at 0° C. for one hour and at room temperature for 1.5 hours
3. extractionThe reaction mixture was extracted twice with ethyl acetate (50 mL)
4. customThe organic phase was separated
5. washwashed with water (10 mL)
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customto give a residue
9. customThe residue was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (20:1

ORD record

ord-575c0d5b5aa04bd0a3ad76a4eebab3e1

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439535B2