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Potassium Hydroxide → 7-Hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid

HRID 1188906
ノート
印刷プレビュー

反応式

HRID 1188906 の反応式
CS([O:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:22]=[N:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17]CC)=[O:16])=[CH:11]2)(=O)=O.[OH-].[K+]>O1CCCC1.C(O)C.O>[OH:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:22]=[N:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 14797Potassium HydroxideHCID 46941746Ethyl 7-[(methylsulfonyl)oxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate

生成物 1

HCID 668976607-Hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid収率 81%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

Ethyl 7-[(methylsulfonyl)oxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (1.56 g) was dissolved in a mixture of tetrahydrofuran (10 mL) and ethanol (15 mL). A solution of potassium hydroxide (85%, 0.8 g) in water (10 mL) was added to the mixture at 0° C. The mixture was allowed to warm to room temperature and stirred for 13 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water and 1M hydrochloric acid (14 mL) was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (0.93 g, 81%) as a pale orange solid. MS 349 (MH+).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. addition1M hydrochloric acid (14 mL) was added to the mixture
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washThe residual solid was washed with diethyl ether

出典と根拠

ORDレコード
ord-75916d9ff96a4237a00ceb9287a10383
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673942B2

反応ノート

読み込み中…

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