N-bromobutanimide → 3-bromo-1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole

HRID 502277Notes

Reaction equation

HRID 502277 reaction equation
[CH:1]1([CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3)[CH:7]=[C:6]2[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH2:3][CH2:2]1.[Br:26]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:26][C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6]=1[C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 590304261-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole

Product 1

HCID 590304283-bromo-1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indoleYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole (200 mg, 0.6 mmol) in DMF (2.5 mL) was added a solution of N-bromosuccinimide (107 mg, 0.6 mmol) in DMF (1.5 mL) dropwise. The reaction mixture was stirred at room temperature for 90 minutes. The reaction mixture was diluted in H2O and extracted with EtOAc. The organic layer was washed with H2O and brine and then dried, concentrated and purified by silica gel chromatography (1:1 CH2Cl2/hexane) to provide 3-bromo-1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole (219 mg, 88%) as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with H2O and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (1:1 CH2Cl2/hexane)

Sources & evidence

ORD record
ord-90b5600b88a04eed955610d645e83bfd
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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