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Potassium Hydroxide → 2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 490455
ノート
印刷プレビュー

反応式

HRID 490455 の反応式
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]([CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[CH:9]=[C:8]2[C:24]1[N:33](S(C2C=CC(C)=CC=2)(=O)=O)[C:27]2=[N:28][CH:29]=[C:30]([F:32])[CH:31]=[C:26]2[CH:25]=1>O.CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]([CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[CH:9]=[C:8]2[C:24]1[NH:33][C:27]2=[N:28][CH:29]=[C:30]([F:32])[CH:31]=[C:26]2[CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 671475492-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 116547592-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine収率 60.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962
Water
溶媒

実験手順

A solution of 2.08 g of potassium hydroxide in 7 ml of water is added to a solution of 0.83 g of 2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1-(toluene-4-sulfonyl)—1H-pyrrolo[2,3-b]pyridine in 100 ml of methanol brought to reflux. The mixture is agitated at reflux for 3 hours 30 minutes. After returning to around 20° C., the mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up with 50 ml of water and extracted with three times 80 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: ethyl acetate/methanol (90/10 by volume)]. 0.37 g of 2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1H-pyrrolo[2,3-b] pyridine is obtained in the form of a solid, the characteristics of which are as follows:

後処理

  1. temperatureto reflux
  2. temperatureat reflux for 3 hours 30 minutes
  3. customAfter returning to around 20° C.
  4. concentrationthe mixture is concentrated to dryness under reduced pressure (13 kPa)
  5. extractionextracted with three times 80 ml of dichloromethane
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  9. customThe residue is purified by flash chromatography on a silica column [eluent: ethyl acetate/methanol (90/10 by volume)]

出典と根拠

ORDレコード
ord-eb29756fda674855883be13cb01c2c28
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07528147B2

反応ノート

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