Potassium Carbonate → Methyl 3-(2-tert-butyl-5-methoxyindol-1-ylmethyl)benzoate

HRID 1191680Notes

Reaction equation

HRID 1191680 reaction equation
O[CH:2]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[NH:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].BrC1C(C)=CC(C)=CC=1C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.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]>[C:24]([C:2]1[N:12]([CH2:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([O:19][CH3:20])=[O:18])[C:5]2[C:4]([CH:3]=1)=[CH:9][C:8]([O:10][CH3:11])=[CH:7][CH:6]=2)([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 684732-BromomesityleneHCID 69670829Methyl 3-{[2-(2-hydroxy-3,3-dimethylbutyl)-4-methoxyphenylamino]methyl}benzoate

Product 1

HCID 69671069Methyl 3-(2-tert-butyl-5-methoxyindol-1-ylmethyl)benzoateYield 67.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of methyl 3-{[2-(2-hydroxy-3,3-dimethylbutyl)-4-methoxyphenylamino]methyl}benzoate (200 mg), 2-bromomesitylene (0.097 mL) and potassium carbonate (148 mg) in N,N-dimethylformamide (5 mL) was added tetrakis(triphenylphosphine)palladium (0) (31.1 mg) at room temperature, and this resulting mixture was stirred at 150° C. for 2 hours under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (127 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4ceb0995bed345b08b356f3cb4b8bb01
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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