Isopropyl iodide → HCID 178458342, compound

HRID 1013839Notes

Reaction equation

HRID 1013839 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:18][CH2:17][C:16]3[C:12](=[CH:13][NH:14][N:15]=3)[CH2:11]2)[C:6]1=[O:19].I[CH:26]([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH:26]([CH3:28])[CH3:27])[CH:21]=[CH:20][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:18][CH2:17][C:16]3[C:12](=[CH:13][NH:14][N:15]=3)[CH2:11]2)[C:6]1=[O:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178515644HCID 178515644, compound

Product 1

HCID 178458342HCID 178458342, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of 3-(2-chloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one (0.2 g, 0.58 mmol) and 2-Iodopropane (0.06 mL, 0.64 mmol) in DMF (4 mL) with potassium carbonate (0.1 g, 0.7 mmol) and stir reaction overnight at room temp. Quench the reaction with 1N HCl and extract with EtOAc. Wash the organic with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography and remove the solvent to afford 0.11 g (48%) of product. MS (m/e): 388 (M+1).

Workup

  1. customreaction overnight at room temp
  2. customQuench
  3. customthe reaction with 1N HCl
  4. extractionextract with EtOAc
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customremove the solvent
  9. customPurify the crude by silica gel column chromatography
  10. customremove the solvent

Sources & evidence

ORD record
ord-e6e220eff38d4711a09fa81e0658c660
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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