2-Chloropyridine → 1-(2-Bromo-3-methylphenyl)-3,4-dihydroisoquinoline

온도

-78 °C

Triflic anhydride (0.18 mL, 1.037 mmol) was added via syringe over 1 min to a stirred mixture of 2-bromo-3-methyl-N-phenethylbenzamide (0.30 g, 0.943 mmol) and 2-chloropyridine (0.11 mL, 1.131 mmol) in DCM (4.7 mL) at −78° C. The reaction mixture was stirred at −78° C. for 5 min, then placed in an ice-water bath and warmed to 0° C. After stirring another 5 min, the solution was allowed to warm to RT and then placed in a pre-heated block and stirred at 45° for 2 h. The reaction mixture was allowed to cool to RT, then it was diluted with 1N NaOH (3 mL) and extracted with DCM (15 mL). The organic extract was washed with saturated aqueous NaCl (2×15 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of 1-10% MeOH/DCM to provide 1-(2-bromo-3-methylphenyl)-3,4-dihydroisoquinoline as off-white glass.

1. customplaced in an ice-water bath
2. temperaturewarmed to 0° C
3. stirringAfter stirring another 5 min
4. temperatureto warm to RT
5. stirringstirred at 45° for 2 h
6. temperatureto cool to RT
7. extractionextracted with DCM (15 mL)
8. extractionThe organic extract
9. washwas washed with saturated aqueous NaCl (2×15 mL)
10. dry with materialdried over Na2SO4
11. filtrationThe solution was filtered
12. concentrationconcentrated in vacuo
13. customto give the crude material as a light-yellow oil
14. customThe crude material was absorbed onto a plug of silica gel
15. custompurified by column chromatography
16. washeluting with a gradient of 1-10% MeOH/DCM

ORD 기록

ord-0b69485dcbef45f2aa0cdf3800d76215

출처 데이터셋

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08735384B2