Water → 6-Nitro-2-phenyl-1H-indole
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([NH:10]C(=O)CCC)[CH:9]=1)([O-:3])=[O:2].CC(C)([O-])C.[K+].O>CN1CCCC1=O>[N+:1]([C:4]1[CH:9]=[C:8]2[C:7]([CH:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of N-(5-nitro-2-(phenylethynyl)phenyl)butyramide (580 mg, 1.88 mmol) in 1-Methyl-2-pyrrolidinone (20 mL) under nitrogen was added potassium tert-butoxide (243 mg, 2.16 mmol). The resulting solution was heated at 70° C. for 6 h, and then left at room temperature for 16 h. Water was added and the aqueous layer was extracted several times with ethyl acetate. The combined organic layers were washed 10 times with water, 3 times with brine, dried over anhydrous MgSO4 and evaporated. The resulting material was purified by column chromatography eluting with ethyl acetate/hexanes 15:85 v/v to afford 175 mg (39%) of the title compound.
Workup
- extractionthe aqueous layer was extracted several times with ethyl acetate
- washThe combined organic layers were washed 10 times with water, 3 times with brine
- dry with materialdried over anhydrous MgSO4
- customevaporated
- customThe resulting material was purified by column chromatography
- washeluting with ethyl acetate/hexanes 15:85 v/v
Sources & evidence
- ORD record
- ord-04af9c92c9eb466a99d6543159a81978
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518980B2
Reaction notes
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