Iodoethane → HCID 11637542, compound

HRID 252522Notes

Reaction equation

HRID 252522 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-6da663c7a5734f1eadf6623e136fc76c
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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