Water → Methyl 1-methyl-3-phenyl-1H-indole-6-carboxylate

HRID 2365366Notes

Reaction equation

HRID 2365366 reaction equation
[H-].[Na+].O[C:4](C(F)(F)F)=O.[C:10]1([C:16]2[C:24]3[C:19](=[CH:20][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CI.O>CN(C=O)C>[CH3:4][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131731077Methyl 3-phenyl-1H-indole-6-carboxylate TFA salt

Product 1

HCID 59626075Methyl 1-methyl-3-phenyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% dispersion in mineral oil, 4.52 mmol, 186 mg) was added portion-wise to a solution of methyl 3-phenyl-1H-indole-6-carboxylate TFA salt 62c (2.07 mmol, 757 mg) in DMF at 0° C. and the mixture was stirred for 20 min. Methyl iodide (2.28 mmol, 0.14 mL) was added and the reaction mixture was maintained at 0° C. for 1 h. Water was then added and the reaction was extracted with EtOAc. The organics were concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give 62d.

Workup

  1. extractionthe reaction was extracted with EtOAc
  2. concentrationThe organics were concentrated
  3. custompurified by flash column chromatography (silica gel, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b9fc4c718dec412590b318274c203cad
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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