Dimethylformamide → HCID 86665747, compound

HRID 1191669Notes

Reaction equation

HRID 1191669 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CN(C)[CH:33]=[O:34].[Cl-].[NH4+]>O1CCCC1.O>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH:33]=[O:34])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 68694614HCID 68694614, compoundHCID 178418339Butyllithium

Product 1

HCID 86665747HCID 86665747, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 minutes and at room temperature for 2 hours
  2. extractionthis resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-184676fb782446d9a3cfbe2ca24be57b
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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