Dimethylformamide → HCID 21360855, compound

HRID 391311Notes

Reaction equation

HRID 391311 reaction equation
[Cl:1][C:2]1[NH:3]C2[C:9]([CH:10]=1)=[CH:8][CH:7]=CN=2.[H-].[Na+].CI.[CH3:15][N:16]([CH:18]=O)[CH3:17]>>[Cl:1][C:2]1[N:3]=[C:15]2[N:16]([CH3:17])[CH:18]=[CH:7][C:8]2=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66787553HCID 66787553, compound

Product 1

HCID 21360855HCID 21360855, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 6 chloro-7-aza indole (1.00 g, 6.55 mmol) in DMF (30 mL) at 0° C. was added sodium hydride (0.524 g, 13.11 mmol) and the mixture was stirred at 0° C. for 20 min. Methyl iodide (0.512 mL, 8.19 mmol) was added at 0° C. and the mixture was warmed to room temperature and stirred for 2 h. The reaction was stopped, quenched with water and extracted with ethyl acetate. The organic layer was washed with water. It was then dried over sodium sulfate and concentrated in vacuo to give 1.01 g of the desires product as a brown color oil. ESI-MS: m/z 167.0 (M+H)+

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for 2 h
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialIt was then dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-537a748c475542c9b3c389611127fe16
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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