Phenylboronic Acid → 6-phenyl-1H-indole

HRID 323843Notes

Reaction equation

HRID 323843 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCO.[Cl-].[Na+].O>[C:11]1([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 6764936-Bromoindole

Product 1

HCID 135858536-phenyl-1H-indoleYield 45.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 6-bromoindole (2.0 g, 10.20 mmol) in anhydrous toluene (20 mL) under a nitrogen atmosphere was treated with Pd[P(Ph3)]4 (10% mol). After stirring the mixture for 30 min., phenylboronic acid (1.87 g, 15.30 mmol) in anhydrous EtOH (10 mL) was added followed by the addition of sat'd NaHCO3 (6 mL). The bi-phasic mixture was heated to reflux for 24 h. After cooling to room temperature, the mixture was added to a sat'd brine solution and extracted with EtOAc (2×). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (1:1 CH2Cl2/heptane) to give the desired material as white powder (900 mg, 45%): 1H NMR (DMSO-d6, 300 MHz) δ 11.15 (br s, 1H), 7.58-7.66 (m, 4H), 7.41-7.47 (m, 2H), 7.36 (m, 1H), 7.26-7.31 (m, 2H), 6.42 (m, 1H).

Workup

  1. temperatureThe bi-phasic mixture was heated
  2. temperatureto reflux for 24 h
  3. extractionextracted with EtOAc (2×)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (1:1 CH2Cl2/heptane)

Sources & evidence

ORD record
ord-defe8f73e0604009b2c67dbbde107da2
Source dataset
uspto-grants-2001_04
Patent number
US06214991B1

Reaction notes

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