Tetrahydrofuran → 5-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid

HRID 1042109ノート

反応式

HRID 1042109 の反応式
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([O:30]CC)=[O:29])=[CH:15]3)=[N:9][CH:10]=1)(=[O:4])=[O:3].[OH-].[Na+].O1CCCC1>C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:20]=2)[NH:17][C:16]([C:28]([OH:30])=[O:29])=[CH:15]3)=[N:9][CH:10]=1)(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66726001HCID 66726001、化合物

生成物 1

HCID 667259135-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid収率 109.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of ethyl 5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylate (4.0 g), 1M aqueous sodium hydroxide solution (13 mL), tetrahydrofuran (20 mL), and ethanol (20 mL) was stirred at 50° C. for 50 min. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in water. 1M Hydrochloric acid (13.2 mL) was added and the precipitated yellow solid was collected by filtration. The obtained solid was washed with water and diethyl ether to give the title compound (4.1 g, yield 100%) as a yellow solid.

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. addition1M Hydrochloric acid (13.2 mL) was added
  4. filtrationthe precipitated yellow solid was collected by filtration
  5. washThe obtained solid was washed with water and diethyl ether

出典と根拠

ORDレコード
ord-cf051521010c4ff18e497f4969966155
出典データセット
uspto-grants-2013_10
特許番号
US08557805B2

反応ノート

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