Hydrochloric Acid → 3-Chloro-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyrid-2-yl)-1H-indole-2-carboxylic acid

HRID 646141Notes

Reaction equation

HRID 646141 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:28][CH:27]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1.O>[Cl:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:18][N:17]=3)[CH:12]=2)[N:7]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:34])[CH3:35])=[CH:28][CH:27]=2)[C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 684751033-Chloro-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyridin-2-yl)indole-2-carboxylic acid ethyl ester

Product 1

HCID 686972133-Chloro-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyrid-2-yl)-1H-indole-2-carboxylic acidYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-chloro-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyrid-2-yl)-1H-indole-2-carboxylic acid ethyl ester (see step (a) above; 500 mg, 1.0 mmol) in dioxane (5 mL) was added NaOH (aq. 2N, 2.5 mL) and the reaction was refluxed for 4 h. After cooling to room temperature, the reaction was diluted with water and acidified by the addition of HCl (aq. 1N) to about pH 6. The precipitate was filtered, washed with water and dried. Recrystallisation (from EtOAc/petroleum ether) afforded the title compound (289 mg, 62%).

Workup

  1. temperaturethe reaction was refluxed for 4 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customRecrystallisation (from EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-d8476b70c30942eaab76ba0289e4b0dd
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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