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

HRID 1042109노트

반응식

HRID 1042109 반응식
[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]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66726001HCID 66726001, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cf051521010c4ff18e497f4969966155
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557805B2

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