Toluene → HCID 22266985, compound

HRID 899026Notes

Reaction equation

HRID 899026 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1B(O)O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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(O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2[S:9][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:11]=2)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 276852,5-Dichloropyridine

Product 1

HCID 22266985HCID 22266985, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

In a 500 ml-three-necked flask, 12.6 g (85.2 mM) of 2,5-dichloropyridine, 15.2 g (85.4 mM) of benzothiophene-2-boronic acid, 75 ml of toluene, 37.5 ml of ethanol and 75 ml of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 3.06 g (2.64 mM) of tetrakis(triphenylphosphine)palladium (0) was added thereto, followed by refluxing under stirring for 8 hours 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, 100 ml of methanol was added and washed under stirring at room temperature, followed by filtration to recover the crystal. The crystal was purified by silica gel column chromatography (eluent: chloroform) and recrystallized from a mixture solvent of chloroform-methanol to obtain 11.8 g (Yield: 56.4%) of 5-chloro-2-(benzo[b]thienyl)pyridine (colorless crystal).

Workup

  1. additionwas added
  2. temperatureby refluxing
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled on an ice bath
  5. customto precipitate a crystal, which
  6. filtrationwas then filtered out
  7. washwashed with water
  8. additionTo the crystal, 100 ml of methanol was added
  9. washwashed
  10. stirringunder stirring at room temperature
  11. filtrationfollowed by filtration
  12. customto recover the crystal
  13. customThe crystal was purified by silica gel column chromatography (eluent: chloroform)
  14. customrecrystallized from a mixture solvent of chloroform-methanol

Sources & evidence

ORD record
ord-5aea286d3c034be2bff566f08f891aeb
Source dataset
uspto-grants-2008_04
Patent number
US07354662B2

Reaction notes

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