N,N'-Dimethylethylenediamine → HCID 57675734, compound

HRID 491023Notes

Reaction equation

HRID 491023 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:19])=[CH:4][CH:3]=1.I[C:21]1C=C[C:24]([N:27]2[C:35]3[C:30](=CC(OC)=CC=3)[CH:29]=[C:28]2C)=[CH:23][CH:22]=1.COC1C=C2C(=CC=1)NC(C)=C2.BrC1C=CC(I)=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([C:21]#[C:22][CH2:23][CH2:24][N:27]3[CH2:35][CH2:30][CH2:29][CH2:28]3)=[CH:3][CH:4]=1)[C:9]([CH3:19])=[CH:10]2

Participants

9

Reactant 6

HCID 8070N,N'-DimethylethylenediamineHCID 115221-Bromo-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 706425-Methoxy-2-methylindoleHCID 57675739HCID 57675739, compoundHCID 59596734HCID 59596734, compound

Product 1

HCID 57675734HCID 57675734, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-Bromophenyl)-5-methoxy-2-methyl-1H-indole and 1-(4-Iodophenyl)-5-methoxy-2-methyl-1H-indole. 5-Methoxy-2-methylindole (500 mg, 3.1 mmol) and 1-bromo-4-iodobenzene (877 mg, 3.1 mmol) were dissolved in toluene (6 mL). To the resulting solution were added copper(I) iodide (12 mg, 0.062 mmol), potassium phosphate tribasic (1.32 g, 6.2 mmol), and N,N′-dimethylethylenediamine (6.6 μL, 0.062 mmol). The mixture was heated at 80° C. overnight, allowed to cool to room temperature and filtered through a pad of silica. The resulting solution was concentrated to give a mixture of both the bromo and the iodo halophenyl indoles, which were used without further purification (assumed quantitative).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through a pad of silica
  3. concentrationThe resulting solution was concentrated
  4. customto give
  5. customthe iodo halophenyl indoles, which were used without further purification (assumed quantitative)

Sources & evidence

ORD record
ord-d6e49752d6754b9eaef1cd74cb5eb478
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Reaction notes

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