6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene → (6-Chloro-pyridin-3-yl)-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophen-3-yl]-methanone

HRID 354069Notes

Reaction equation

HRID 354069 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[S:18][C:17]=2[CH:29]=1.[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([C:20]2[C:16]3[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:29][C:17]=3[S:18][C:19]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 27821656-Chloronicotinoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23512898(6-Chloro-pyridin-3-yl)-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophen-3-yl]-methanoneYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-Chloropyridine-5-carbonyl chloride (4.23 gm, 24 mmol) and 6-Methoxy-2-(4-methoxy-phenyl) -benzo[b]thiophene (5.0 gm, 18.5 mmol) in 275 mL of methylene chloride was added aluminum trichloride (18.59 g, 138.8 mmol) in three portions. The black-red reaction was stirred for 16 hrs. at room temperature. The reaction was then quenched with 400 mL of 2N NaOH (slowly and cooled in ice) and extracted into 300 mL of methylene chloride. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to a yellow solid which was chromatographed on silica gel using 5% to 20% Ethyl acetate/Hexanes as the gradient eluant to yield 2.47 gm of the title compound.

Workup

  1. customThe black-red reaction
  2. customat room temperature
  3. customThe reaction was then quenched with 400 mL of 2N NaOH (slowly and
  4. temperaturecooled in ice) and
  5. extractionextracted into 300 mL of methylene chloride
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to a yellow solid which
  10. customwas chromatographed on silica gel using 5% to 20% Ethyl acetate/Hexanes as the gradient eluant

Sources & evidence

ORD record
ord-7931cbc65c364b249cb01a240934fdec
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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