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

HRID 1809973Notes

Reaction equation

HRID 1809973 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-816922fac15a49fa84be5e8518b87631
Source dataset
uspto-grants-2013_01
Patent number
US08362055B2

Reaction notes

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