Methyl iodide → HCID 23087237, compound

HRID 2423665Notes

Reaction equation

HRID 2423665 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[N+:20]([O-])=O)[NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:25]I>CN(C)C=O.O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[N:9]([CH3:25])[C:10]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)=[C:13]([NH2:20])[CH:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57934145HCID 57934145, compound

Product 1

HCID 23087237HCID 23087237, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methoxy-2-(4-methoxy-2-nitrophenyl)-1H-indole (1.0 g) in N,N-dimethylformamide (10 ml) was added 60% sodium hydride (160 mg) on an ice bath. The solution was stirred for 20 minutes at room temperature, then methyl iodide (570 mg) was added dropwise thereto on an ice bath, and the solution was stirred for 2 hours at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. Obtained by purifying the residue by NH silica gel column chromatography (hexane-ethyl acetate system), the total amount of 6-methoxy-2-(4-methoxy-2-nitrophenyl)-1-methyl-1H-indole was used according to an analogous synthetic method to Example 22 to provide the title compound (720 mg).

Workup

  1. stirringon an ice bath, and the solution was stirred for 2 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customObtained
  7. customby purifying the residue by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-6d39f40752fe4229aea61fba31cc70a5
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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