Water → HCID 67291579, compound

HRID 511838Notes

Reaction equation

HRID 511838 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]2)=[CH:5][CH:4]=1.IC.[C:21](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:21][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([C:2]([F:17])([F:1])[F:18])[CH:11]=2)[CH:7]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22311001Ethyl 6-(trifluoromethyl)-1H-indole-2-carboxylate

Product 1

HCID 67291579HCID 67291579, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 6-(trifluoromethyl)-1H-indole-2-carboxylate (100 mg, 0.39 mmol), iodomethane (36 microL, 0.58 mmol), and potassium carbonate (134 mg, 0.97 mmol) in DMF was stirred at room temperature for 7 hours. Then, the mixture was poured into water, and the aqueous layer was extracted with dichloromethane (three times). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (20:1-10:1) to give 95.3 mg (90% yield) of the title compound as a white solid:

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane (three times)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (20:1-10:1)

Sources & evidence

ORD record
ord-c79bb5d60f5f490ca7a8a20040a78417
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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