Methyl iodide → HCID 9880949, compound

HRID 2184928Notes

Reaction equation

HRID 2184928 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:26])[CH2:5][CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:24][CH3:25])[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:9].I[CH3:28]>CN(C=O)C.O>[CH3:26][N:4]([CH3:3])[CH2:5][CH2:6][CH2:7][C:8]([N:10]([C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:24][CH3:25])[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:28])=[O:9]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9901766HCID 9901766, compound

Product 1

HCID 9880949HCID 9880949, compoundYield 5.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (8 mg of a 60% suspension in mineral oil, 4 mg, 0.19 mmol, 1.2 equiv) was added to a solution of 4-dimethylamino-N-(9-ethyl-9H-carbazol-3-yl)-butyramide (50 mg, 0.15 mmol, 1 equiv) in DMF (0.3 mL). The resultant suspension was stirred at room temperature for 1 hour, and then iodomethane (0.012 mL, 27 mg, 0.19 mmol, 1.25 equiv) was added via syringe. After an additional 5 hours at room temperature, the reaction mixture was diluted with water (5 mL) and extracted with ethyl acetate (3×5 mL). The combined extracts were washed with water (1×10 mL) and brine (1×10 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by rotary chromatography (CH2Cl2 grading to 2% ammonium hydroxide in 5% MeOH/CH2Cl2) to provide 4-dimethylamino-N-(9-ethyl-9H-carbazol-3-yl)-N-methyl-butyramide (3 mg, 5%) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washThe combined extracts were washed with water (1×10 mL) and brine (1×10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by rotary chromatography (CH2Cl2 grading to 2% ammonium hydroxide in 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2388b7461ff1435fbbbba62c3985ed67
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

Loading…