Hydrochloric Acid → 5-(4-Tert-Butylphenyl)-1-[4-(Propan-2-Yloxy)phenyl]-1h-Indole-2-Carboxylic Acid

HRID 646095Notes

Reaction equation

HRID 646095 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[CH:27][CH:26]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].O.Cl>O1CCOCC1>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH:32]([CH3:33])[CH3:34])=[CH:29][CH:30]=2)[C:6]([C:4]([OH:5])=[O:3])=[CH:14]3)=[CH:16][CH:17]=1)([CH3:22])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 687003415-(4-tert-Butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

Product 1

HCID 115101785-(4-Tert-Butylphenyl)-1-[4-(Propan-2-Yloxy)phenyl]-1h-Indole-2-Carboxylic AcidYield 67.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-(4-tert-butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (259 mg, 0.57 mmol; see step (b)), NaOH (114 mg, 2.85 mmol), water (0.6 mL) and dioxane (3 mL) was heated using microwave irradiation for 1 h at 120° C. An additional portion of NaOH (100 mg) was added and heating was continued for another 30 min at 120° C. After cooling, the reaction was acidified with HCl (1M) to pH 2 and extracted with EtOAc. The combined extracts were washed with water, brine and dried over Na2SO4 and purified by chromatography to give the title compound (165 mg, 60%).

Workup

  1. temperaturewas heated
  2. custommicrowave irradiation for 1 h at 120° C
  3. temperatureheating
  4. temperatureAfter cooling
  5. extractionextracted with EtOAc
  6. washThe combined extracts were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-2a1fb2db2e2f46a8a4901dd2ca331eb6
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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