Thioacetamide → 5-Bromo-2-(2-methyl-1,3-thiazol-4-yl)pyridine

温度

75 °C

2-bromo-1-(5-bromopyridin-2-yl)ethanone (3.77 g, 13.5 mmol) was dissolved in ethanol (32 mL) and ethanethioamide (1.12 g, 14.8 mmol) was added and the reaction stirred for 18 h at 75° C. The mixture was concentrated; the residual solid was dispersed in ethyl acetate (100 mL), and treated with saturated sodium bicarbonate solution (100 mL) until no further gas evolution was noted. The combined organics were washed with water (50 mL) and brine (50 mL). The aqueous washes were back-extracted with ethyl acetate (100 mL) and the combined organic layers were dried over magnesium sulfate, treated with Darco, filtered through a paper filter, and concentrated to give a yellow solid. The crude product was purified by flash chromatography (90 g silica gel, 1-5% methanol in ethyl acetate). The major product was further purified by flash chromatography (40 g silica gel, 10% ethyl acetate in hexane) to give the title compound (1.94 g) as a colorless crystalline solid.

1. concentrationThe mixture was concentrated
2. additionthe residual solid was dispersed in ethyl acetate (100 mL)
3. additiontreated with saturated sodium bicarbonate solution (100 mL) until no further gas evolution
4. washThe combined organics were washed with water (50 mL) and brine (50 mL)
5. extractionThe aqueous washes were back-extracted with ethyl acetate (100 mL)
6. dry with materialthe combined organic layers were dried over magnesium sulfate
7. additiontreated with Darco
8. filtrationfiltered through a paper
9. filtrationfilter
10. concentrationconcentrated
11. customto give a yellow solid
12. customThe crude product was purified by flash chromatography (90 g silica gel, 1-5% methanol in ethyl acetate)
13. customThe major product was further purified by flash chromatography (40 g silica gel, 10% ethyl acetate in hexane)

ORDレコード

ord-f0d2dfff92514fd3a99f4d00ab0f9297

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09227971B2