Dimethylformamide → HCID 14064740, compound

HRID 878782Notes

Reaction equation

HRID 878782 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:23][CH3:24])[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 78518Ethyl 5-chloroindole-2-carboxylate

Product 1

HCID 14064740HCID 14064740, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-chloro-1H-indole-2-carboxylate (500 mg, 2.17 mmol), potassium carbonate (450 mg, 3.25 mmol), iodoethane (260 μL, 3.25 mmol) and N,N-dimethylformamide (10.8 mL) was stirred at room temperature for 3 days. To the reaction solution was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water three times, and the organic layer was filtered through diatomaceous earth, followed by silica gel, and then the filtrate was concentrated under reduced pressure to give ethyl 5-chloro-1-ethyl-1H-indole-2-carboxylate (566 mg, 100%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washwashed with water three times
  3. filtrationthe organic layer was filtered through diatomaceous earth
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-19097f7c5c944bf0a2f9b0532a1a3b4b
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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