Iodoethane → 1-ETHYL-1H-INDOLE-5-CARBONITRILE

HRID 1481685Notes

Reaction equation

HRID 1481685 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:14](I)[CH3:15]>CN(C=O)C>[CH2:14]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

Product 1

HCID 117081311-ETHYL-1H-INDOLE-5-CARBONITRILEYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indole-5-carbonitrile (2.0 g, 14.1 mmol) in DMF (30 mL) was added NaH (60% suspension in mineral oil, 0.81 g, 20.3 mmol, 1.4 eq) at 0° C. The mixture was stirred at 0° C. for 30 min before EtI (1.35 mL, 16.9 mmol, 1.2 eq) was added. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with H2O then extracted by Et2O (3×40 mL). The combined organic layers were washed with H2O (50 mL) then dried over Na2SO4. The solvent was removed to afford crude product (2.57 g, ca. 14.1 mmol) which was used in the next step without further purification.

Workup

  1. additionwas added
  2. customThe reaction was quenched with H2O
  3. extractionthen extracted by Et2O (3×40 mL)
  4. washThe combined organic layers were washed with H2O (50 mL)
  5. dry with materialthen dried over Na2SO4
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-7415680391c948f8b8745a89485f993b
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…