Iodine → HCID 59381950, compound

HRID 2354570Notes

Reaction equation

HRID 2354570 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[CH:17]3)[CH:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[I:32]I.[O-]S([O-])(=S)=O.[Na+].[Na+].[H-].[Na+].[C:43]1([S:49](Cl)(=[O:51])=[O:50])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([S:49]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)(=[O:51])=[O:50])[CH:18]=[C:17]3[I:32])[CH:10]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 6

HCID 807IodineHCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 59381926HCID 59381926, compound

Product 1

HCID 59381950HCID 59381950, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-benzyl-4-(1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.17 g, 0.4 mmol) in 2.5 mL DMF was added powdered KOH (0.060 g, 1.1 mmol), followed by I2 (0.11 g, 0.4 mmol) in DMF. The solution was stirred for 45 minutes and then treated with 10% aqueous Na2S2O3. The mixture was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was immediately taken up in 2 mL DMF and treated with 60% NaH (0.02 g, 0.5 mmol). After 20 minutes the solution was treated with benzenesulfonyl chloride (0.07 mL, 0.5 mmol). After 30 minutes of stirring the mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with H2O, washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification via flash chromatography (30% EtOAc in hexanes) afforded 4-(1-benzenesulfonyl-3-iodo-1H-indol-5-yl)-3-benzyl-piperazine-1-carboxylic acid tert-butyl ester (0.23 g, 83%) as a white foam; MS (M+H)=658.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. stirringAfter 30 minutes of stirring the mixture
  6. customwas quenched with H2O
  7. extractionextracted with EtOAc
  8. washThe combined organic layers were washed with H2O
  9. washwashed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customPurification via flash chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4b58b8709cbc48829120680130075e4b
Source dataset
uspto-grants-2010_07
Patent number
US07754721B2

Reaction notes

Loading…