Dimethylformamide → HCID 59453843, compound

HRID 1662045Notes

Reaction equation

HRID 1662045 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:17]N(C=O)C.[H-].[Na+].CI>O>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH3:17])[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13574130HCID 13574130, compound

Product 1

HCID 59453843HCID 59453843, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 3-acetyl-1H-indole-6-carboxylate (0.92 g) and DMF (18 ml) was added sodium hydride (0.18 g) under ice-cooling, followed by stirring at room temperature for 0.5 hour. Next, methyl iodide (0.29 ml) was added thereto under ice-cooling, followed by stirring at room temperature for 5 hours. Then, water was added thereto under ice-cooling, followed by stirring at room temperature. The solid precipitated was collected by filtration, washed with water, and purified by silica gel column chromatography (hexane/THF=2:1→chloroform /THF=9:1) to obtain methyl 3-acetyl-1-methyl-1H-indole-6-carboxylate (0.98 g).

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature for 5 hours
  4. temperatureunder ice-cooling
  5. stirringby stirring at room temperature
  6. customThe solid precipitated
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. custompurified by silica gel column chromatography (hexane/THF=2:1→chloroform /THF=9:1)

Sources & evidence

ORD record
ord-22ae9083a27d4cf7bd947e08ce8794c2
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

Loading…