Dimethylformamide → HCID 57476000, compound

HRID 1994706Notes

Reaction equation

HRID 1994706 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:6]2.[H-].[Na+].CN(C)C=O.[CH3:26][O:27][CH2:28]Cl>O1CCCC1.C(OCC)(=O)C>[CH3:26][O:27][CH2:28][N:6]1[C:7]2[C:3](=[C:2]([CH3:1])[CH:10]=[CH:9][C:8]=2[N+:11]([O-:13])=[O:12])[CH:4]=[C:5]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 12301124Ethyl 4-methyl-7-nitro-1H-indole-2-carboxylate

Product 1

HCID 57476000HCID 57476000, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 4-methyl-7-nitro-1H-indole-2-carboxylate (7.0 g), 60% sodium hydride (1.35 g) and N,N-dimethylformamide (40 ml) was stirred at room temperature for 30 min. This solution was ice-cooled, and a solution of chloromethyl methyl ether (2.6 ml) in tetrahydrofuran (15 ml) was added dropwise. The mixture was stirred at 4° C. for 4 hr, and the reaction solution was diluted with ethyl acetate, washed with saturated brine, aqueous citric acid solution and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=5:95-1:5) to give the title compound (5.6 g, yield 68%) as pale-yellow needle crystals.

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at 4° C. for 4 hr
  3. washwashed with saturated brine, aqueous citric acid solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-934e6b805a944265ac919a4e8f4aa0db
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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