Tetrahydrofuran → 5-(2-methoxyethoxy)-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylic acid

HRID 504773ノート

反応式

HRID 504773 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)(=[O:18])=[O:17])[CH:14]=1)[NH:11][C:10]([C:25]([O:27]CC)=[O:26])=[CH:9]2.O1CCCC1.[OH-].[K+]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)(=[O:17])=[O:18])[CH:14]=1)[NH:11][C:10]([C:25]([OH:27])=[O:26])=[CH:9]2

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 57476206ethyl 5-(2-methoxyethoxy)-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylate

生成物 1

HCID 574762055-(2-methoxyethoxy)-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylic acid収率 84.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of ethyl 5-(2-methoxyethoxy)-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylate (5.40 g), tetrahydrofuran (50 mL) and methanol (50 mL) was added a 85% aqueous solution (30 mL) of potassium hydroxide (3.0 g), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated, aqueous citric acid solution was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and concentrated to give a white solid. The obtained solid was washed with a mixed solvent of ethyl acetate-hexane to give the title compound (4.24 g, yield 84%) as colorless crystals. melting point 230-232° C.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionaqueous citric acid solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. concentrationconcentrated
  6. customto give a white solid
  7. washThe obtained solid was washed with a mixed solvent of ethyl acetate-hexane

出典と根拠

ORDレコード
ord-a56d370b4f0c4c708b702421c977e70b
出典データセット
uspto-grants-2010_08
特許番号
US07777047B2

反応ノート

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