Hydrochloric Acid → 5-phenyl-1H-indole

HRID 1827984Notes

Reaction equation

HRID 1827984 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[C:14]1([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 27343615-Indolylboronic acid

Product 1

HCID 114582105-phenyl-1H-indoleYield 67.9%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of indole-5-boronic acid (2.0 g, 12.4 mmole); iodobenzene (2.48 g, 12.2 mmole), tetrakis(triphenylphosphine) palladium (0) (288 mg, 0.25 mmole), sodium carbonate (4.34 g, 40.9 mmole) in water (20 ml), and dioxane (20 ml) was stirred under an argon atmosphere and heated to 100° C. for 5 hrs, cooled to room temperature, acidified with 1M HCl, extracted, washed, dried, and evaporated. The residue was purified by chromatography to give about 1.6 g of 5-phenyl-1H-indole, mp. 72–74° C.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-96ba3f538ab24323931c82217f60243f
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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