Dimethylformamide → 5-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole

HRID 2089566Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([Cl:19])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:9]2)([O-:3])=[O:2].P(Cl)(Cl)(OCl)=O.CN([CH:29]=[O:30])C>ClCCl>[Cl:19][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:9]2[CH:29]=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

7-Nitro-5-chloro-2-phenyl-1H-indole (1.0 g, 3.67 mmol) prepared in Preparation 26 was dissolved in dichloromethane (20 mL). Phosphoryloxychloride (0.84 g, 5.50 mmol) and DMF (0.80 g, 11.01 mmol) were added in drops thereto at 0° C., and the mixture was stirred for 6 h at room temperature. After completion of the reaction, the reaction was quenched by saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was 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 (0.5 g, Yield 45%).

Workup

customAfter completion of the reaction
customthe reaction was quenched by saturated aqueous sodium hydrogen carbonate solution
extractionThe reaction mixture was extracted with ethyl acetate
washwashed with saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-c9eb85bacddc4b1eb4eb48d1a0abd931
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436038B2

Reaction notes

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