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

HRID 502271Notes

Reaction equation

HRID 502271 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.[I:26]N1C(=O)CCC1=O>CN(C=O)C.O>[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)[C:7]([I:26])=[C:6]2[C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 590304261-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole

Product 1

HCID 590304301-cyclopropylmethyl-6-ethoxy-3-iodo-2-(4-nitro-phenyl)-1H-indoleYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole (800 mg, 2.38 mmol) in DMF (8.6 mL) at room temperature was added a solution of N-iodosuccinimide (585 mg, 2.6 mmol) in DMF (5.6 mL) dropwise. The reaction mixture was stirred at room temperature for 2 h, diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O, and then with sat. aq. NaHCO3 and then dried and concentrated. The residue was triturated with hexane to provide 1-cyclopropylmethyl-6-ethoxy-3-iodo-2-(4-nitro-phenyl)-1H-indole (1.061 g, 96%) as an orange solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with H2O
  3. dry with materialwith sat. aq. NaHCO3 and then dried
  4. concentrationconcentrated
  5. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-ef63cffdb6094c3198ec2dfd6daf034c
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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