Dimethylformamide → HCID 12043493, compound

HRID 2184935Notes

Reaction equation

HRID 2184935 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:25])[CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[H-].[Na+].CI.[CH3:30]N(C=O)C>C1COCC1.CCOC(C)=O>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([N:16]([CH3:30])[C:17](=[O:25])[CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22458803HCID 22458803, compound

Product 1

HCID 12043493HCID 12043493, compoundYield 2.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-(9-Ethyl-9H-carbazol-3-yl)-2-pyridin-3-yl-acetamide (329 mg, 0.899 mmol) in THF at 0° C. was added NaH (60% oil dispersion, 86 mg, 2.158 mmol), then the cooling bath removed. After stirring an additional 25 minutes methyl iodide (67 μl, 1.08 mmol) was added, and the reaction mixture stirred overnight. A portion of DMF (4 ml) was then added and stirring continued for several hours. The reaction mixture was then diluted with EtOAc and the organic layer washed with saturated aq. NaHCO3, H2O, and brine, dried (Na2SO4), and concentrated to afford the crude product as a brown oil. Chromatographic purification (silica, 10% MeOH/CH2Cl2) afforded the desired product (7 mg, 2.2% yield). MS m/z @ 344 (m+1).

Workup

  1. customthe cooling bath removed
  2. additionwas added
  3. stirringstirring
  4. waitcontinued for several hours
  5. washthe organic layer washed with saturated aq. NaHCO3, H2O, and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto afford the crude product as a brown oil
  9. customChromatographic purification (silica, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cbd1c23b0b01441f8f7345d8fadd88cf
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

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