N-bromobutanimide → HCID 57426225, compound

HRID 641438Notes

Reaction equation

HRID 641438 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][NH:8]2)([O-:3])=[O:2].[Br:19]N1C(=O)CCC1=O>CC(O)=O>[Br:19][C:7]1[NH:8][C:9]2[C:5]([C:6]=1[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57426224HCID 57426224, compound

Product 1

HCID 57426225HCID 57426225, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of ethyl (4-nitro-1H-indol-3-yl)acetate from Step A (1.00 g, 4.03 mmol) in AcOH (40 mL) was added N-bromosuccinimide (789 mg, 4.43 mmol) in AcOH (40 mL) dropwise over 30 min. The resulting mixture was stirred at ambient temperature for 1 h, then concentrated to dryness under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CHCl3:EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=327 (M+1).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe crude product was purified by silica gel chromatography
  3. washeluting with a gradient of CHCl3

Sources & evidence

ORD record
ord-c1e1fdfe46804ff5b54abba256efb7d3
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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