Dimethylformamide → HCID 57476000, compound

HRID 1851384Notes

Reaction equation

HRID 1851384 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. The solution was ice-cooled, and a solution (15 mL) of chloromethyl methyl ether (2.6 mL) in tetrahydrofuran was added dropwise. The mixture was stirred at 4° C. for 4 hr, and the reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution, water and saturated brine, 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 aqueous citric acid solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3e413ffd4f34cb9bc7f913d863c3fec
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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