Dimethylformamide → HCID 57901758, compound

HRID 1851380Notes

Reaction equation

HRID 1851380 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=1)[N:7]([CH2:20][O:21][CH3:22])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2.[H-].[Na+].[CH3:30]N(C)C=O.CI>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N:11]([CH3:30])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:14])[CH:10]=1)[N:7]([CH2:20][O:21][CH3:22])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57901661HCID 57901661, compound

Product 1

HCID 57901758HCID 57901758, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of ethyl 5-fluoro-1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.45 g), 60% sodium hydride (52 mg) and N,N-dimethylformamide (10 mL) was stirred at 4° C. for 30 min. Methyl iodide (0.095 mL) was added to the solution, and the mixture was stirred at room temperature for 2 days. The reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution 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=1:9-2:8) to give the title compound (0.20 g, yield 43%) as colorless prism crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 days
  2. washwashed with aqueous citric acid solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4712b702876048e3a894b0b3e6c81ea0
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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