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

HRID 1728617ノート

反応式

HRID 1728617 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dd5b8316be9a405891f0ded22d8ba01f
出典データセット
uspto-grants-1994_07
特許番号
US05328920

反応ノート

読み込み中…