Toluene → 6-(4-Methoxyphenyl)-1-tert-butoxycarbonylindole

HRID 2210598Notes

Reaction equation

HRID 2210598 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O-])([O-])=[O:19].[Na+].[Na+].[C:24]1(C)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][O:19][C:24]1[CH:29]=[CH:28][C:27]([C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[CH:9][N:8]3[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:12][CH:13]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 114493211-BOC-6-Bromoindole

Product 1

HCID 112095106-(4-Methoxyphenyl)-1-tert-butoxycarbonylindoleYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-6-bromoindole (5.0 g, 17 mmol) in toluene (200 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.94 g, 0.84 mmol), 2N aqueous Na2CO3 (100 mL), and a solution of 4-methoxyboronic acid in ethanol (50 mL). The 2-phase mixture was heated at 110°-125° C. for two hours. The reaction mixture was cooled to ambient temperature and the layers where separated. The aqueous phase was extracted twice with ether. The combined organic layers where washed twice with brine, dried over MgSO4, filtered, and concentrated in vacuo to give a brown oil. Chromatography on silica gel (250 g, 5% ether, hexanes) afforded 6-(4-methoxyphenyl)-1-tert-butoxycarbonylindole (3.2 g, 58%).

Workup

  1. temperatureThe 2-phase mixture was heated at 110°-125° C. for two hours
  2. customthe layers where separated
  3. extractionThe aqueous phase was extracted twice with ether
  4. washThe combined organic layers where washed twice with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil

Sources & evidence

ORD record
ord-390eb436e1a94e56bb699e45659c11dc
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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