Ethanol → HCID 66657785, compound

HRID 420934Notes

Reaction equation

HRID 420934 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:28][CH:27]=2)[C:7]=1[CH2:36][C:37]([O:39]CC)=[O:38])=[O:5])[CH3:2].[OH-].[Na+].CCO>O>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:30][CH:31]=2)[C:7]=1[CH2:36][C:37]([OH:39])=[O:38])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66657631HCID 66657631, compound

Product 1

HCID 66657785HCID 66657785, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(4-isopropoxyphenyl)-2-ethoxycarbonylmethyl-5-(5-trifluoromethyl-2-pyridinyloxy)indole-3-carboxylic acid ethyl ester (260 mg, 0.46 mmol, see step (a) above), NaOH (aq, 1 M, 1.4 mL) and EtOH (2 mL) was stirred at 50° C. for 2.5 h, cooled, diluted with H2O (4 mL), washed with EtOAc and acidified to pH 5 with citric acid (aq, 1 M) and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), concentrated and purified by chromatography. Yield 144 mg (58%).

Workup

  1. temperaturecooled
  2. washwashed with EtOAc
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-1236376f76924f0ca46f7bead7ff376b
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

Loading…