Dimethylformamide → HCID 57901678, compound

HRID 1851386Notes

Reaction equation

HRID 1851386 reaction equation
[F: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>[F: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])[N:6]2[CH2:26][O:27][CH3:28]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 53399265HCID 53399265, compound

Product 1

HCID 57901678HCID 57901678, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of ethyl 4-fluoro-7-nitro-1H-indole-2-carboxylate (0.48 g), 60% sodium hydride (0.12 g) and N,N-dimethylformamide (20 mL) was stirred at 4° C. for 30 min. A solution (5 mL) of chloromethyl methyl ether (0.25 mL) in tetrahydrofuran was added dropwise under ice-cooling. After stirring at room temperature for 18 hr, 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=1:5) to give the title compound (0.46 g, yield 81%) as pale-brown needle crystals.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for 18 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-9986c8183cb5449b8360c8ace67646b6
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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