Imidazole → 5-((Tert-butyldimethylsilyloxy)methyl)-2-fluoropyridine

(6-Fluoropyridin-3-yl)methanol (9.54 g, 75.0 mmol) and imidazole (5.11 g, 75.0 mmol) were placed into a round-bottomed flask with CH2Cl2 (300 mL). tert-butyldimethylsilyl chloride (10.9 g, 72.8 mmol) was dissolved in CH2Cl2 (75 mL) and added drop-wise to the reaction mixture, which was then allowed to stir overnight at rt. The reaction was quenched by adding water (100 mL). The biphasic mixture was then separated and the aqueous layer was washed with CH2Cl2 (2×30 mL). The combined organic layer was then washed with H2O (3×50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrated to give 5-((tert-butyldimethylsilyloxy)methyl)-2-fluoropyridine as a yellow oil, which was used in the next step without further purification.

1. additionadded drop-wise to the reaction mixture, which
2. customThe reaction was quenched
3. additionby adding water (100 mL)
4. customThe biphasic mixture was then separated
5. washthe aqueous layer was washed with CH2Cl2 (2×30 mL)
6. washThe combined organic layer was then washed with H2O (3×50 mL), brine (50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-b07d70777e4e41ad8635dbb2de8cffeb

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791147B2