Sodium Hydroxide → 5-((6-Chloropyrimidin-4-yl)oxy)-1H-indole

HRID 2264564

反応式

HRID 2264564 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[CH:16][N:15]=1>O.CC(C)=O>[Cl:13][C:14]1[N:15]=[CH:16][N:17]=[C:18]([O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH:19]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 160545-HydroxyindoleHCID 709434,6-Dichloropyrimidine

生成物 1

HCID 574551565-((6-Chloropyrimidin-4-yl)oxy)-1H-indole

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
-10 °C

実験手順

5-Hydroxyindole (91.8 g, 0.69 mol) is added in portions to a stirred solution of NaOH (27.9 g, 0.69 mol) in water (560 m L) at 10° C., to give a solution which is then cooled to −10° C. A solution of 4,6-dichloropyrimidine (95.3 g, 0.63 mol) in acetone (560 mL) is then added over a period of 65 min. The mixture is stirred at 0° C. for 30 min and then the acetone is evaporated off under reduced pressure, to give a mixture which is extracted with CH2Cl2. The combined extracts are washed with cold aqueous NaOH (0.5 M), dried (Na2SO4) and the solvent is evaporated off under reduced pressure to afford the product to afford the crude product which is purified by chromatography (silica gel; eluent 10% EtOAc in CH2Cl2) and recrystallised from CH2Cl2—hexane to give the title compound as a colourless crystalline solid, m.p. 149-150° C. Utilising a similar procedure, but employing 2,4-dichloropyrimidine in lieu of 4,6-dichloropyrimidine afforded 5-[(2-chloro-4-pyrimidinyl)oxy]-1H-indole, as cream crystalline solid, m.p. 169-176° C.

後処理

  1. customto give a solution which
  2. customthe acetone is evaporated off under reduced pressure
  3. customto give a mixture which
  4. extractionis extracted with CH2Cl2
  5. washThe combined extracts are washed with cold aqueous NaOH (0.5 M)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent is evaporated off under reduced pressure
  8. customto afford the product
  9. customto afford the crude product which
  10. customis purified by chromatography (silica gel; eluent 10% EtOAc in CH2Cl2)
  11. customrecrystallised from CH2Cl2—hexane

出典と根拠

ORDレコード
ord-58b2835193fc4b0ab8c730d030f6fccb
出典データセット
uspto-grants-2010_12
特許番号
US07855215B2

関連ノート

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