Methyl iodide → HCID 9839348, compound

HRID 1167228Notes

Reaction equation

HRID 1167228 reaction equation
[CH3:1][CH:2]([CH3:20])[CH2:3][NH:4][C:5](=[O:19])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:7].[CH3:21][Si]([N-][Si](C)(C)C)(C)C.[Na+].IC>CN(C)C=O.O1CCCC1.O>[CH3:21][N:4]([CH2:3][CH:2]([CH3:20])[CH3:1])[C:5](=[O:19])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:7]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 9795926HCID 9795926, compound

Product 1

HCID 9839348HCID 9839348, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 0.3 g (1.0 mmol) of N-2-methylpropyl-2-(4-(3-thienyl)phenyl)propionamide (prepared in example 12) in 5 mL of dimethylformamide was added 1.1 mL (1.1 mmol) of 1.0 M sodium bis(trimethylsilyl)amide in tetrahydrofuran. The mixture was stirred for 10 minutes whereupon 0.2 g (1.1 mmol) of iodomethane was added and the mixture stirred at room temperature for 16 hours. The mixture was diluted with 5 mL of water and extracted three times with 5 mL each of dichloromethane. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Chromatography (10 g silica gel, 20% ethyl acetate/hexanes) afforded 0.2 g (75%) of the title compound.

Workup

  1. additionwas added
  2. extractionextracted three times with 5 mL each of dichloromethane
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1325cd6d38694054acef9230613f323a
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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