Sodium hydride → HCID 86587689, compound

HRID 1836660Notes

Reaction equation

HRID 1836660 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][C:20]([N:22]([O:24][CH3:25])[CH3:23])=[O:21])[CH:16]=2)[CH:11]=[CH:10]1>C1COCC1>[CH3:25][O:24][N:22]([CH3:23])[C:20]([CH:19]1[CH2:2][CH:18]1[C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][NH:9]2)=[CH:13][CH:14]=1)=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 73990723HCID 73990723, compound

Product 1

HCID 86587689HCID 86587689, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Trimethylsulfoxonium iodide (2.20 g, 10.00 mmol) was added to a suspension of sodium hydride (60% dispersion in oil, 0.40 g, 10.00 mmol) in anhydrous THF and stirred at room temperature for 1 h. 3-(1H-Indol-6-yl)-N-methoxy-N-methyl-acrylamide (0.90 g, 3.90 mmol) was dissolved in anhydrous THF and added dropwise to the cloudy white suspension. The mixture was stirred for 16 h at room temperature. The reaction was quenched with a solution of saturated ammonium chloride. Water was added and the solution was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 2-(1H-indol-6-yl)-cyclopropanecarboxylic acid methoxy-methyl-amide as a yellowish solid (0.96 g, 100%). LCMS: MH+: 245.12, 72% AP.

Workup

  1. additionadded dropwise to the cloudy white suspension
  2. stirringThe mixture was stirred for 16 h at room temperature
  3. customThe reaction was quenched with a solution of saturated ammonium chloride
  4. additionWater was added
  5. extractionthe solution was extracted with methylene chloride
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d276f3d11d614179b6bb55619b01808c
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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