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

HRID 1466478Notes

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-d21f37f80e3044ca96c055590a9f99ab
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000028B2

Reaction notes

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