Ammonium Chloride → 1-Allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid

HRID 244437Notes

Reaction equation

HRID 244437 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:33][CH:34]=[CH2:35])[CH:8]=[C:9]([C:11]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:21]=[CH:20]3)([OH:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=1)=[O:5])C.[Cl-].[NH4+]>CCO.[OH-].[Na+].O>[CH2:33]([N:7]1[CH:8]=[C:9]([C:11]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:21]=[CH:20]3)([OH:16])[C:12]([F:14])([F:15])[F:13])[CH:10]=[C:6]1[C:4]([OH:5])=[O:3])[CH:34]=[CH2:35]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 249590981-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 249590961-Allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid ethyl ester (728 mg, 1.5 mmol) in 5 mL of EtOH and 30 mL of 3 M NaOH was stirred at room temperature. After 18 hours, the mixture was neutralized with saturated aqueous ammonium chloride, diluted with water, and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 660 mg (96%) of the title compound as a beige solid. MS m/z 460.25 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fc37001d39c4a379ac92f4ff87c4e1f
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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