Iodoethane → HCID 11160681, compound

HRID 1384800Notes

Reaction equation

HRID 1384800 reaction equation
[F: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.I[CH2:17][CH3:18]>CN(C)C=O>[CH2:17]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:18]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 11160681HCID 11160681, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(washed beforehand with petroleum ether) and of 15 g (72.4 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate in 100 ml of dimethylformamide is stirred for 2 h at room temperature. 7.5 ml (93.7 mmol) of iodoethane, in solution in 20 ml of dimethylformamide, are subsequently added. After stirring for 10 h at room temperature, the reaction mixture is poured onto ice-cold water. It is extracted with diethyl ether. The organic phase is washed several times with water, dried over magnesium sulphate and concentrated under reduced pressure. 17 g (72 mmol) of a yellow oil are obtained, which oil is used as is in the following stage.

Workup

  1. stirringAfter stirring for 10 h at room temperature
  2. additionthe reaction mixture is poured onto ice-cold water
  3. extractionIt is extracted with diethyl ether
  4. washThe organic phase is washed several times with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70a98ba291c040b68862e556899bd791
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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