Phenylboronic Acid → HCID 22266986, compound

HRID 488706Notes

Reaction equation

HRID 488706 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)=[N:6][CH:7]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C1(C)C=CC=CC=1>[S:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:7][N:6]=2)=[CH:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]1=2

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 22266985HCID 22266985, compound

Product 1

HCID 22266986HCID 22266986, compoundYield 20.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342152-(Di-tert-butylphosphino)biphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a 100 ml-three-necked flask, 4.91 g (20.0 mM) of 5-chloro-2-(benzo[b]thienyl)pyridine, 3.66 g (30.0 mM) of phenylboronic acid, 9.58 g (40.0 mM) of tripotassium phosphate hydrate, 3.2 mg (0.020 mM) of palladium (II) acetate, 11.9 mg (0.040 mM) of 2-ditert-butylphosphinobiphenyl and 60 ml of toluene were placed and refluxed under stirring for 24 hours at 100° C. under nitrogen stream. After the reaction, the reaction mixture was cooled on an ice bath to precipitate a crystal, which was then filtered out and washed with water. To the crystal, 25 ml of methanol was added and washed under stirring at room temperature, followed by recovery by filtration. The crystal was purified by silica gel column chromatography (eluent: chloroform) and recrystallized from a chloroform-methanol mixture solvent to obtain 1.17 g (Yield: 20.4%) of 2-(benzo[b]thienyl)-5-phenylpyridine (colorless crystal).

Workup

  1. temperaturerefluxed
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled on an ice bath
  4. customto precipitate a crystal, which
  5. filtrationwas then filtered out
  6. washwashed with water
  7. additionTo the crystal, 25 ml of methanol was added
  8. washwashed
  9. stirringunder stirring at room temperature
  10. filtrationfollowed by recovery by filtration
  11. customThe crystal was purified by silica gel column chromatography (eluent: chloroform)
  12. customrecrystallized from a chloroform-methanol mixture solvent

Sources & evidence

ORD record
ord-35180354c38a4652b8669f6f0d8da9ae
Source dataset
uspto-grants-2005_12
Patent number
US06974639B2

Reaction notes

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