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

HRID 1728617노트

반응식

HRID 1728617 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dd5b8316be9a405891f0ded22d8ba01f
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05328920

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