Ammonium Chloride → 1-(2-(6-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one

HRID 1400908ノート

反応式

HRID 1400908 の反応式
[F:1][C:2]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]4[CH2:26][CH2:25][CH2:24][C:23]4=[O:27])=[CH:16][CH:15]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CCO.[Zn].[Fe]>[NH2:32][C:30]1[CH:29]=[CH:28][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[N:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]5[CH2:26][CH2:25][CH2:24][C:23]5=[O:27])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:31]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 584745171-(2-(6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one

生成物 1

HCID 584747051-(2-(6-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one収率 46%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 23994Zinc触媒HCID 702Ethanol溶媒

実験手順

To impure 293 (0.76 g, 1.6 mmol) in EtOH (75 mL) was added zinc dust (1.04 g, 15.9 mmol), iron filings (0.89 g, 16 mmol) and saturated aqueous ammonium chloride solution (2 mL). The resultant mixture was heated to reflux for 18 h, then cooled, filtered through celite, concentrated and re-dissolved in dichloromethane. The solution was washed with water, 1 M NaOH, and brine, dried (anhydrous MgSO4), filtered, concentrated and the residue was purified by silica gel chromatography (15% MeOH/chloroform) to afford title compound 294 (0.33 g, 46% yield). MS (M+H): 449.2

後処理

  1. temperatureto reflux for 18 h
  2. temperaturecooled
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. dissolutionre-dissolved in dichloromethane
  6. washThe solution was washed with water, 1 M NaOH, and brine
  7. dry with materialdried (anhydrous MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was purified by silica gel chromatography (15% MeOH/chloroform)

出典と根拠

ORDレコード
ord-d6481775f9194642b5f4ce310f0cdc52
出典データセット
uspto-grants-2014_12
特許番号
US08906852B2

反応ノート

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