Chlorotrimethylsilane → HCID 22940220, compound

Temperature

-78 °C

In dry tetrahydrofuran (15 mL) was dissolved 498 mg (1.70 mmol) of 3-(2-tert-butylphenoxy)-6-chloro-4-methoxypyridazine obtained in Example 31 (1), the solution was cooled to −78° C., 1.10 mL (1.87 mmol) of a n-butyl lithium-hexane solution (1.70M) was added to the solution and the resulting mixture was stirred for 20 minutes. To the mixture was added 0.370 mL (2.91 mmol) of trimethylsilyl chloride, and the resulting mixture was stirred at the same temperature for 10 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, extracted with ether. The organic layers were combined, washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography to obtain 596 mg (1.63 mmol, Yield: 95.9%) of 3-(2-tert-butylphenoxy)-6-chloro-4-methoxy-5-(trimethylsilyl)pyridazine.

1. addition1.10 mL (1.87 mmol) of a n-butyl lithium-hexane solution (1.70M) was added to the solution
2. stirringthe resulting mixture was stirred at the same temperature for 10 minutes
3. extractionextracted with ether
4. washwashed successively with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was removed
7. customthe obtained residue was purified by silica gel column chromatography

ORD record

ord-1b6a9f3caff340b3b3ffc1333082c32a

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964531B2