Sodium hydride → HCID 57422597, compound

To a suspension of sodium hydride (to which about 40% of a mineral oil was added, 0.23 g) in N,N-dimethylformamide (10 mL), 5-bromo-2-hydroxy-4-methylpyridine (1.00 g) was added under ice-cooling and the resultant reaction mixture was stirred for 30 minutes. To the reaction mixture, 3-hydroxy-3-methylbutyl 4-methylbenzene sulfonate (1.51 g) was added and the resultant reaction mixture was stirred at 60° C. for 4 hours. To the reaction mixture, a aqueous solution of saturated ammonium chloride was added and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67) to obtain the subject compound (0.92 g) as a light yellow oil.

1. additionwas added
2. temperaturecooling
3. customthe resultant reaction mixture
4. customthe resultant reaction mixture
5. stirringwas stirred at 60° C. for 4 hours
6. customthe resultant reaction mixture
7. extractionwas extracted with ethyl acetate
8. washThe organic phase was washed with saturated saline
9. dry with materialwas dried over anhydrous sodium sulfate
10. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
11. customthe resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67)

ORD record

ord-91a0ba1013584c779780840da3477c52

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476287B2