Nitromethane → (E)-4-chloro-3-(2-nitrovinyl)-1H-indole

A mixture of 4-chloroindole-3-carbaldehyde (314 mg, 1.75 mmol) and ammonium acetate (404 mg, 5.25 mmol) in nitromethane (6 mL) was stirred at 100° C. for 20 min. The reaction mixture was cooled, diluted with water and extracted with EtOAc (2×40 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crude material was purified by silicagel column chromatography (50-100% EtOAc/heptane) to give compound B19-1 (224 mg, 58%) as an orange solid.

1. temperatureThe reaction mixture was cooled
2. extractionextracted with EtOAc (2×40 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure
6. customThe crude material was purified by silicagel column chromatography (50-100% EtOAc/heptane)
7. customto give compound B19-1 (224 mg, 58%) as an orange solid

ORD-Eintrag

ord-667568d9aac94626bb7287d0d56df59a

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09365522B2