Iodoethane → 1-Ethyl-1H-indole-5-carbonitrile
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
Product 1
Reagents, catalysts & solvents 1
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.