Water → HCID 87077397, compound

Temperature

-70 °C

To a reaction container equipped with a dropping funnel, 21.6 g of 2,5-dibromopyridine and 243 mL of diethyl ether were added. The obtained solution was cooled at −70° C. and then, 56.63 mL of butyl lithium (1.61 M/hexane solution) was added dropwise thereto. The obtained mixture was stirred for 1 hour and 25 minutes and then, a solution obtained by dissolving 20.96 mL of tert-butyldimethylsilyl trifluoromethanesulfonate in 16.7 mL of diethyl ether was added dropwise thereto. The obtained mixture was stirred for 4 hours and 30 minutes and then, 162 mL of water was added dropwise thereto at 0° C. The obtained mixture was stirred at room temperature overnight and then, 81 mL of ethyl acetate was added thereto. The obtained solution was extracted three times with 81 mL of ethyl acetate. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography and recrystallized using hexane to obtain 1 g of 2-bromo-5-tert-butyldimethylsilylpyridine. Purity: 95% (area percentage value obtained by gas chromatography analysis).

1. customTo a reaction container equipped with a dropping funnel
2. customa solution obtained
3. additionwas added dropwise
4. stirringThe obtained mixture was stirred for 4 hours and 30 minutes
5. customat 0° C
6. stirringThe obtained mixture was stirred at room temperature overnight
7. extractionThe obtained solution was extracted three times with 81 mL of ethyl acetate
8. additionThe obtained organic layers were mixed
9. dry with materialdried with magnesium sulfate
10. customAfter removing magnesium sulfate
11. filtrationby filtration
12. concentrationthe filtrate was concentrated
13. customto obtain a crude product
14. customThe crude product was purified with silica gel column chromatography
15. customrecrystallized

ORD record

ord-61d4349579d549dc99a1fdab1134720b

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088883B2