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

HRID 376876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376876
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 193601686-Fluoro-3-(3-fluoro-4-pyridinylamino)benzo[b]thiopheneAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c3eb8ab11ada4254a7df3fdb70623f4e
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022880

Notizen zur Reaktion

Wird geladen…