Bromobenzene → HCID 22144629, compound

HRID 1824996Notes

Reaction equation

HRID 1824996 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cu](Br)Br>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 22144629HCID 22144629, compound

Reagents, catalysts & solvents 1

HCID 24611Copper bromide (CuBr2)Catalyst

Conditions

Temperature
156 °C

Procedure

5.5 g (22.31 mmol) of ethyl 5-nitro-1H-indole-2-carboxylate, 6.16 g (44.62 mmol) of anhydrous potassium carbonate, 77.53 g (52 ml, 493.8 mmol) of bromobenzene and 1.6 g (11.15 mmol) of copper bromide are stirred under reflux (about 156° C.) for 5 days. The reaction mixture is then filtered, and the residue on the frit is washed with toluene. The collected filtrates are concentrated, dried under high vacuum and purified by flash chromatography on silica gel.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. washthe residue on the frit is washed with toluene
  3. concentrationThe collected filtrates are concentrated
  4. customdried under high vacuum
  5. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-970354bfb7394b9a9e4bd8f6e3f6b19d
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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