Sodium Carbonate → 1h-Indole-3-acetic acid,2-phenyl-,ethyl ester

HRID 2187630Notes

Reaction equation

HRID 2187630 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(=O)([O-])[O-].[Na+].[Na+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCOCC1.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>[C:23]1([C:2]2[NH:3][C:4]3[C:9]([C:10]=2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 53994886Ethyl (2-bromo-1H-indol-3-yl)acetate

Product 1

HCID 125026691h-Indole-3-acetic acid,2-phenyl-,ethyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.0 g (7.1 mmol) of ethyl (2-bromoindol-3-yl)acetate in 40 ml of dioxane was added under argon 1.2 g (0.11 mmol) of Pd(PPh3)4 and 13.3 ml of 2.0 M sodium carbonate. After stirring at room temperature for ca. 15 min, 1.3 g (11 mmol) of benzeneboronic acid was added, and the mixture was heated at 80° C. under argon overnight. The mixture was cooled to room temperature and solids were removed by filtration. The filtrate was concentrated and chromatographed on silica gel with toluene as an eluent to yield 1.6 g (81%) of the 2-phenyl indole as a yellow crystalline solid.

Workup

  1. temperaturethe mixture was heated at 80° C. under argon overnight
  2. temperatureThe mixture was cooled to room temperature
  3. customsolids were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customchromatographed on silica gel with toluene as an eluent

Sources & evidence

ORD record
ord-fd2b2434d51e4ab8bdf44da49d132eb7
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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