Hydrochloric Acid → HCID 66658114, compound

HRID 420999Notes

Reaction equation

HRID 420999 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=2)[C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:12][C:11]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[C:17]([CH2:16][CH2:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][N:23]=3)[CH:12]=2)[N:7]([C:32]2[CH:33]=[CH:34][C:35]([O:38][CH:39]([CH3:40])[CH3:41])=[CH:36][CH:37]=2)[C:6]=1[C:4]([OH:5])=[O:3])([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66657709HCID 66657709, compound

Product 1

HCID 66658114HCID 66658114, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(2-ethoxycarbonylethyl)-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyridin-2-yl)indole-2-carboxylic acid ethyl ester (150 mg, 0.26 mmol; see step (d) above), NaOH (aq, 1 M, 2.5 mL) and dioxane (4 mL) was heated at 90° C. for 1 h, cooled, acidified with HCl (aq, 1 M) to pH 2 and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to give the title compound. Yield 50 mg (38%).

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-b283c1e02a314e9bbc3e6d859a841cd8
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

Loading…