Indole → 2-Phenylpyridine

HRID 1160031Notes

Reaction equation

HRID 1160031 reaction equation
CC(C)([O-])C.[Na+].F[C:8]1[CH:13]=[C:12](F)[CH:11]=[CH:10][C:9]=1[C:15]1[CH:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=1.N1C2C(=CC=CC=2)C=C1.C1(C)C=CC=CC=1>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:8]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 798Indole2×HCID 1140TolueneHCID 23676156Sodium t-butoxideHCID 686459024-Chloro-2-(2,4-difluorophenyl)pyridine

Product 1

HCID 138872-PhenylpyridineYield 126%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 6344DichloromethaneSolvent

Procedure

44.9 mg (0.2 mmol) of palladium acetate, 70 mg (0.2 mmol) of 2-(dicyclohexylphosphino)biphenyl, 1.3455 grams (14 mmol) of sodium t-butoxide, 1.1281 grams (5 mmol) of 2-(2,4-difluorophenyl)-4-chloropyridine, and 0.7029 grams (6 mmol) of indole were mixed with 60 ml of toluene and refluxed for 48 hours. Next a double portion of the catalyst package and one more portion of indole was added to the mixture to reflux for 72 hours. The reaction contents were cooled to room temperature, diluted with dichloromethane and preabsorbed onto silica and chromatographed using methylene chloride eluent to isolate 0.978 grams of yellow solid in 63% yield.

Workup

  1. temperaturerefluxed for 48 hours
  2. temperatureto reflux for 72 hours
  3. customThe reaction contents
  4. custompreabsorbed onto silica
  5. customchromatographed

Sources & evidence

ORD record
ord-23c56ae5a265462d94daf1039cd93230
Source dataset
uspto-grants-2010_10
Patent number
US07816016B1

Reaction notes

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