Iodoethane → HCID 11637542, compound

HRID 907129Notes

Reaction equation

HRID 907129 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) was added dropwise a solution of 3-phenyl-5-nitroindole (40.0 mg, 2.1 mmol) in DMF (0.75 mL). The reaction mixture was stirred for 20 min at 0° C. under N2. Ethyl iodide (14.8 μL, 0.185 mmol) was added dropwise and the reaction mixture was stirred for an additional 3 hours. The reaction mixture was diluted with water (250 mL), and extracted with EtOAc (30 mL). The organic phase was washed with water (250 mL) and was then dried over MgSO4 and the solvent was removed in vacuo. The desired N-ethyl-3-phenyl-5-nitroindole was obtained as a yellow powder (40.0 mg, 89.5% yield).

Workup

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

Sources & evidence

ORD record
ord-c0ed9335276b4d8093cc74c893580932
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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