Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 68694614 | HCID 68694614 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86665747 | HCID 86665747 | — |
Reaction Steps
To a solution of 1-benzenesulfonyl-5-bromo-2-phenylindole (958 mg) in tetrahydrofuran (11.6 mL) was added dropwise n-butyllithium (2.76 mol/L hexane solution, 0.84 mL) at −78° C. under an argon atmosphere, and the mixture was stirred for 30 minutes. Then N,N-dimethylformamide (0.535 mL) was added dropwise, and the mixture was stirred at −78° C. for 30 minutes and at room temperature for 2 hours. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (225 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680120B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-184676fb782446d9a3cfbe2ca24be57b |
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| Source note | uspto-grants-2014_03 |
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