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

HRID 1802824Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][C:3]=1I.[C:13]1([C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Li+].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:11][C:5]1[CH:4]=[C:3]2[C:2](=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=1)[NH:1][C:20]([Si:21]([CH3:24])([CH3:22])[CH3:23])=[C:19]2[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Amino-5-chloro-3-nitro-phenyliodide (1.5 g, 4.90 mmol) obtained in Step 1 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL), and thereto 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. The mixture was heated under stirring for 3 hours at 100° C. At the end of reaction, added water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give 5-chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole (1.05 g, Yield 87%).

Workup

temperatureThe mixture was heated
customAt the end of reaction
extractionextracted with ethylacetate
washThe extract was washed with saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was removed under reduced pressure
customthe residue was separated by column chromatography

Sources & evidence

ORD record: ord-5461f0e0cb0b41a48773a002496e998f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349885B2

Reaction notes

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