Sodium hydride → tert-Butyl 2-(6-nitro-1H-indol-1-yl)acetate

NaH (4.5 mmol, 1.5 equiv.) was suspended in DMF (5 ml), and 6-nitro-indole (3 mmol, 1 equiv.), dissolved in DMF (5 ml), was added at 0° C. The mixture was stirred for 30 min. Then tert-butyl bromoacetate (3.6 mmol, 1.2 equiv.) was added and the mixture was stirred for 15 h at 25° C. The reaction mixture was hydrolysed with ammonium chloride and extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with water and sat. NaCl solution (in each case 20 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography. Yield: 47%

1. additionwas added at 0° C
2. stirringthe mixture was stirred for 15 h at 25° C
3. extractionextracted with ethyl acetate (3×20 ml)
4. washThe combined organic phases were washed with water and sat. NaCl solution (in each case 20 ml),
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by column chromatography

ORD 기록

ord-72655f08ffef4a4cafbdce7b6f6bacb6

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08492559B2