Pyrrolidine → HCID 58790077、化合物

HRID 418609ノート

反応式

HRID 418609 の反応式
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[F:28])[CH:10]=2)=[CH:5][CH:4]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CC(O)C>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:8][CH:7]=3)[S:17][C:16]=12

参加物

4

反応物 2

HCID 31268PyrrolidineHCID 594245202-(4-(Chloromethyl)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

生成物 1

HCID 58790077HCID 58790077、化合物収率 45%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a suspension of 52 (444 mg, 0.98 mmol, crude material from the previous step) in iPrOH (10 ml) was added pyrrolidine (210 mg, 2.96 mmol) and the reaction mixture was refluxed for 4 hrs. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The solution was washed with water and the organic layer was collected, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated and the resultant oil was purified by column chromatography (eluents EtOAc to 30% MeOH in EtOAc), to afford title compound 53 (200 mg, 45% yield) as an orange solid. MS (m/z): 450.2 (M+H).

後処理

  1. temperaturethe reaction mixture was refluxed for 4 hrs
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe solution was washed with water
  5. customthe organic layer was collected
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customthe resultant oil was purified by column chromatography (eluents EtOAc to 30% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-3ded23a015c641e381cc2811f3216666
出典データセット
uspto-grants-2012_01
特許番号
US08093264B2

反応ノート

読み込み中…