Acetone → (3-iodopropyl)-1H-indole

HRID 1751008Notes

Reaction equation

HRID 1751008 reaction equation
[I-:1].[Na+].CC1C=CC(S(OCCC[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)(=O)=O)=CC=1.[CH3:26][C:27]([CH3:29])=O>>[I:1][CH2:26][CH2:27][CH2:29][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:18]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 151749063-(1H-indol-3-yl)propyl 4-methylbenzenesulfonate

Product 1

HCID 11323600(3-iodopropyl)-1H-indole

Procedure

Sodium iodide (827 mg, 5.52 mmol, 2 equiv) was added to a solution of 3-(1H-indol-3-yl)propyl 4-methylbenzenesulfonate (909 mg, 2.76 mmol, 1 equiv) in acetone, and the mixture was refluxed for 16 h. Upon cooling the reaction, it was evaporated under reduced pressure and the residue was taken into dichloromethane. The organic layer was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, Rf=0.7, gradient—5%-30% ethyl acetate in hexanes) to afford the title compound as an oil (789 mg, quant); 1H NMR (400 MHz, DMSO-d6): δ 2.07-2.14 (m, 2H); 2.78 (t, 2H, J=7.6 and 6.8 Hz); 3.29 (t, 2H, J=6.8 Hz); 6.95-6.99 (m, 1H); 7.04-7.08 (m, 1H); 7.14 (d, 1H, J=2 Hz); 7.32-7.34 (m, 1H); 7.52 (d, 1H, J=8 Hz); 10.81 (s, 1H); MS for C11H12IN m/z 285.12 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. temperatureUpon cooling
  3. customthe reaction, it
  4. customwas evaporated under reduced pressure
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude mixture was purified

Sources & evidence

ORD record
ord-eba93e96311b48469a294f11fbf064b6
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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