Isopropyl iodide → HCID 23003233, compound

HRID 396515Notes

Reaction equation

HRID 396515 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[H-].[Na+].I[CH:28]([CH3:30])[CH3:29]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH:28]([CH3:30])[CH3:29])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 23003512HCID 23003512, compound

Product 1

HCID 23003233HCID 23003233, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl[6-chloro-2-(4-hydroxybenzoyl)-1H-indol-3-yl]acetate (Example 183, 0.15 g, 0.44 mmol) in DMF (5 ml) was added sodium hydride (15 mg, 0.46 mmol) at room temperature under nitrogen atmosphere. After 5min., 2-iodopropane (78 mg) was added and the mixture was stirred for 7 h. The mixture was quenched with 2N aqueous HCl (20 ml), and extracted with ethyl acetate (50 ml). The extract was washed with water (30 ml) and brine (30 ml), dried (MgSO4), and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate-hexane (1:2) to afford 72 mg (43%) of the title compound as white solids.

Workup

  1. customThe mixture was quenched with 2N aqueous HCl (20 ml)
  2. extractionextracted with ethyl acetate (50 ml)
  3. washThe extract was washed with water (30 ml) and brine (30 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. washeluting with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-b4c15aa0f64c4a7cac0d09940af6f193
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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