Water → 6-Fluoro-3-(3-fluoro-4-pyridinylamino)benzo[b]thiophene

HRID 1728617Notes

Reaction equation

HRID 1728617 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:4]=2[S:5][CH:6]=1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[F:20].O>CN1CCCC1=O>[F:11][C:8]1[CH:9]=[CH:10][C:3]2[C:2]([NH:1][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[F:20])=[CH:6][S:5][C:4]=2[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 107971626-Fluorobenzo[b]thiophen-3-amineHCID 193602344-Chloro-3-fluoropyridine hydrochloride

Product 1

HCID 193601686-Fluoro-3-(3-fluoro-4-pyridinylamino)benzo[b]thiopheneYield 82.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-amino-6-fluorobenzo[b]thiophene (10 g, 60 mmol) and 4-chloro-3-fluoropyridine hydrochloride (12 g, 71 mmol) in 150 mL of 1-methyl-2-pyrrolidinone was stirred at 90°-95° for 2.5 h, and thereafter cooled, stirred with water and extracted with ether. The aqueous layer was basified with 30% aqueous ammonium hydroxide and extracted with ether. The organic extract was washed with water and saturated sodium chloride solution, and dried (anhydrous magnesium sulfate), filtered and concentrated to give 13 g of a solid. Elution through silica with 10% ethyl acetate in dichloromethane via flash column chromatography yielded 7 g (44.6%) of a white solid, mp 155°-157° C. Recrystallization of 2 g from acetonitrile afforded 1.3 g (29%) of white needles, mp 158°-159° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. extractionextracted with ether
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride solution
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd5b8316be9a405891f0ded22d8ba01f
Source dataset
uspto-grants-1994_07
Patent number
US05328920

Reaction notes

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