Triethylamine → 5-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole

2-Amino-5-chloro-3-nitro-phenyliodide (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100□. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%).

1. temperatureunder heating for 3 h to 100□
2. additionwas added to the reaction mixture, which
3. extractionwas then extracted with ethyl acetate
4. washwashed with saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customThe solvent was removed under reduced pressure
8. customthe residue was purified by column chromatography

ORD record

ord-b1ed735a68b042d390336cad4c215686

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000028B2