Ethyl Acetate → 1-Ethyl-2-methyl-6-nitro-1H-indole

HRID 2079915Notes

Reaction equation

HRID 2079915 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[CH3:15])[CH3:2].[Br:16]NC(=O)CCC(N)=O.C(OCC)(=O)C>C1COCC1>[Br:16][C:5]1[C:6]2[C:11](=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[N:3]([CH2:1][CH3:2])[C:4]=1[CH3:15].[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[CH3:15])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 9834204N-BromosuccinamideHCID 574422751-Ethyl-2-methyl-6-nitro-1H-indole

Product 2

HCID 574422751-Ethyl-2-methyl-6-nitro-1H-indoleHCID 574422763-Bromo-1-ethyl-2-methyl-6-nitro-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of 1-ethyl-2-methyl-6-nitro-1H-indole, 19 (0.36 g, 1.76 mmol) and N-bromosuccinamide (0.31 g, 1.76 mmol) in anhydrous THF (10 mL) under inert atmosphere at ambient temperature for 14 hours. Quench the reaction with saturated aqueous sodium bicarbonate, add ethyl acetate, and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous brine. Dry the organic layer over sodium sulfate, filter, and concentrate in vacuo. Chromatograph over silica gel using hexanes/ethyl acetate (9:1) to afford the title compound and unreacted 1-ethyl-2-methyl-6-nitro-1H-indole (0.37 g) in a 4:1 mixture which can be used in the subsequent step without further purification. LRMS (API ES+)=: 283, 285 (M, M+2M).

Workup

  1. customQuench
  2. customthe reaction with saturated aqueous sodium bicarbonate
  3. washwash with saturated aqueous sodium bicarbonate
  4. dry with materialDry the organic layer over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-dad918eb68694517adb403b8109f7365
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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