Water → 7-Methoxy-4-nitro-1-(propan-2-yl)-1H-indole

HRID 240911Notes

Reaction equation

HRID 240911 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2.[H-].[Na+].I[CH:18]([CH3:20])[CH3:19].O>CN(C=O)C.C(OCC)(=O)C>[CH:18]([N:10]1[C:11]2[C:7](=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=[CH:4][C:3]=2[O:2][CH3:1])[CH:8]=[CH:9]1)([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 17954765HCID 17954765, compound

Product 1

HCID 534141937-Methoxy-4-nitro-1-(propan-2-yl)-1H-indole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methoxy-4-nitro-1H-indole (S) (1 eq) in DMF cooled in an ice bath was added NaH (60% dispersion in oil, 1.2 eq). The reaction was stirred for 1 hr at room temperature then recooled in an ice bath. 2-Iodopropane (1.1 eq) was added then the reaction was stirred for 2 hrs at room temperature. Water and ethyl acetate were added. The ethyl acetate layer was separated and washed repeatedly (3×) with water. The ethyl acetate layer was concentrated then evaporated to dryness. Further purification by column chromatography produced the pure desired product.

Workup

  1. customthen recooled in an ice bath
  2. stirringthe reaction was stirred for 2 hrs at room temperature
  3. customThe ethyl acetate layer was separated
  4. washwashed repeatedly (3×) with water
  5. concentrationThe ethyl acetate layer was concentrated
  6. customthen evaporated to dryness
  7. customFurther purification by column chromatography

Sources & evidence

ORD record
ord-66e96dbb9ff74822b3dceaafa446b5b4
Source dataset
uspto-grants-2014_02
Patent number
US08648104B2

Reaction notes

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