Water → HCID 66657812, compound

HRID 420926Notes

Reaction equation

HRID 420926 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]=[CH:18][CH:17]=3)[CH:13]=2)[N:8]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)[C:7]=1[CH2:38][C:39]([O:41]CC)=[O:40])=[O:5])C.[OH-].[Na+].O>CCO>[C:39]([CH2:38][C:7]1[N:8]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=2)[C:9]2[C:14]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:13][C:12]([O:15][C:16]1[C:25]3[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=1)=[CH:11][CH:10]=2)([OH:41])=[O:40]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66657613HCID 66657613, compound

Product 1

HCID 66657812HCID 66657812, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(7-chloroquinolin-4-yloxy)-2-ethoxycarbonylmethyl-1-(4-trifluoromethoxyphenyl)indole-3-carboxylic acid ethyl ester (40 mg, 0.065 mmol, see step (a) above), NaOH (50 mg), water (1 mL) and EtOH (1 mL) was heated at reflux for 1 h. The EtOH was removed in vacuo and the mixture was acidified with HCl (aq, 1 M) to pH 4. The solid was filtered off to give the title compound. Yield 33 mg (91%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customThe EtOH was removed in vacuo
  4. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-67186341941f4973a6c6d4493db3b49f
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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