Sodium Hydroxide → 4-{1-[2-(3-Fluoro-phenyl)-ethylamino]-indan-5-yloxy}-benzamide

HRID 422253ノート

反応式

HRID 422253 の反応式
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[CH2:25][CH2:26][NH2:27].[OH-].[Na+]>CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C.Cl[Ti](Cl)(Cl)Cl.C1COCC1>[F:21][C:22]1[CH:23]=[C:24]([CH2:25][CH2:26][NH:27][CH:2]2[C:10]3[C:5](=[CH:6][C:7]([O:11][C:12]4[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=4)=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)[CH:28]=[CH:29][CH:30]=1

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 5339282-(3-Fluorophenyl)ethanamineHCID 597506634-(1-Oxo-indan-5-yloxy)-benzamide2 回

生成物 1

HCID 597506524-{1-[2-(3-Fluoro-phenyl)-ethylamino]-indan-5-yloxy}-benzamide収率 6%

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 178460666HCID 178460666、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a round bottom flask, combine 4-(1-Oxo-indan-5-yloxy)-benzamide (Intermediate 24, 45.0 mg, 0.17 mmol), m-Fluorophenethylamine (33 uL, 0.25 mmol), THF (5 mL), and Ti(OiPr)4 (0.1 mL, 0.27 mmol) at 0° C. under nitrogen atmosphere. Stir the reaction for 3 hours then add TiCl4 (0.3 mL, 0.27 mmol) at 0° C. For the next 2 hours, warm the reaction to room temperature and then add BH3SMe2 (0.09 mL, 0.17 mmol). Stir the reaction at room temperature for 12 hours, then add 1N NaOH (aq) and stir for 2 hours. Centrifuge and decant the reaction into a separatory funnel and wash the organic phase with water and dry over Na2SO4. Concentrate the reaction under reduced pressure and purify using reverse phase chromatography (5% to 95% 0.001% TFA buffer in acetonitrile/water) to afford 3.5 mg, 0.01 mmol (6% yield) of the title compound:

後処理

  1. customIn a round bottom flask, combine
  2. customat 0° C.
  3. customthe reaction for 3 hours
  4. customat 0° C
  5. temperatureFor the next 2 hours, warm
  6. customthe reaction to room temperature
  7. stirringStir
  8. customthe reaction at room temperature for 12 hours
  9. stirringstir for 2 hours
  10. customCentrifuge and decant
  11. customthe reaction into a separatory funnel
  12. washwash the organic phase with water
  13. dry with materialdry over Na2SO4
  14. concentrationConcentrate
  15. customthe reaction under reduced pressure
  16. custompurify

出典と根拠

ORDレコード
ord-07bffc67f95544c983657d49ec884165
出典データセット
uspto-grants-2012_01
特許番号
US08101638B2

反応ノート

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