Potassium Carbonate → ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate

HRID 1169355Notes

Reaction equation

HRID 1169355 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20](OB(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1.C(O)C.O>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]3)=[CH:4][CH:3]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70094966-Bromo-1H-indole-2-carboxylic acid ethyl esterHCID 190353504-Methylphenyl dihydrogen borate

Product 1

HCID 22990151ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylateYield 75.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of ethyl 6-bromo-1H-indole-2-carboxylate (2.5 g) and 4-methylphenylboric acid (1.39 g), potassium carbonate (2.58 g) and toluene/ethanol/water (90/9/9 ml) was stirred at room temperature for one hour. Into the reaction mixture was added tetrakis(triphenylphosphine)palladium (0.32 g), and the resulting mixture was heated at reflux for 18 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate/hexane 1:5→1:2→1:1) and to recrystallization (ethyl acetate/hexane) to obtain ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate (1.92 g) as colorless crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialwas dried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was subjected to purification
  9. customto recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-09fb8bc2a9b44f5e965601581d9830ee
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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