Indole → N-(4-methylphenyl)indole

HRID 496928Notes

Reaction equation

HRID 496928 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.Cl[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 798IndoleHCID 78104-ChlorotolueneHCID 10796Cesium carbonate

Product 1

HCID 9794286N-(4-methylphenyl)indoleYield 89%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

An oven-dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (11.6 mg, 0.012 mmol, 5 mol % Pd), 2 [Example 1] (11.0 mg, 0.028 mmol, 5.5 mol %), Cs2CO3 (230 mg, 0.75 mmol) and indole (60 mg, 0.51 mmol). The tube was purged with argon then toluene (1.0 mL) and 4-chlorotoluene (60 μL, 0.51 mmol) were added through a rubber septum. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at 100° C. for 24 h. The reaction was then diluted with ether (20 mL), filtered through celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 94 mg (89%) of a colorless oil.

Workup

  1. customAn oven-dried resealable Schlenk tube was purged with argon
  2. customThe tube was purged with argon
  3. customThe septum was removed
  4. customthe tube was sealed with a teflon
  5. customscrew cap
  6. additionThe reaction was then diluted with ether (20 mL)
  7. filtrationfiltered through celite and
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-08e084f3ff874c09bbe8001d70902dd6
Source dataset
uspto-grants-2005_09
Patent number
US06946560B2

Reaction notes

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