Iodoethane → HCID 11637542, compound

HRID 506029Notes

Reaction equation

HRID 506029 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=3)[NH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:21](I)[CH3:22]>CN(C=O)C.O>[CH2:21]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:10]1)[CH3:22]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 6171745-Nitro-3-phenyl-1H-indole

Product 1

HCID 11637542HCID 11637542, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 60% NaH in mineral oil (8.7 mg, 0.630 mmol) and DMF (1.0 mL) is added dropwise a solution of 3-phenyl-5-nitroindole (40.0 mg, 2.1 mmol) in DMF (0.75 mL). The reaction mixture is stirred for 20 min at 0° C. under N2. Ethyl iodide (14.8 μL, 0.185 mmol) is added dropwise and the reaction mixture is stirred for an additional 3 hours. The reaction mixture is diluted with water (250 mL), and extracted with EtOAc (30 mL). The organic phase is washed with water (250 mL) and is then dried over MgSO4 and the solvent is removed in vacuo. The desired N-ethyl-3-phenyl-5-nitroindole is obtained as a yellow powder (40.0 mg, 89.5% yield).

Workup

  1. stirringthe reaction mixture is stirred for an additional 3 hours
  2. extractionextracted with EtOAc (30 mL)
  3. washThe organic phase is washed with water (250 mL)
  4. dry with materialis then dried over MgSO4
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-79789de95cbd4b7293cabf604455817b
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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