2-Mercaptobenzoic Acid → 4-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole

HRID 383461Notes

Reaction equation

HRID 383461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](SC)=[C:10]2[C:20]2[C:21]([CH3:26])=[N:22][O:23][C:24]=2[CH3:25])=[CH:5][CH:4]=1.SC1C=CC=CC=1C(O)=O.FC(F)(F)C(O)=O.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]2[C:20]2[C:21]([CH3:26])=[N:22][O:23][C:24]=2[CH3:25])=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 583782154-(1-(4-Methoxyphenyl)-3-(methylthio)-1H-indol-2-yl)-3,5-dimethylisoxazole

Product 1

HCID 583782004-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazoleYield 86%

Procedure

4-(1-(4-Methoxyphenyl)-3-(methylthio)-1H-indol-2-yl)-3,5-dimethylisoxazole (the intermediate product of step (c) from the synthesis of Example 21, 140 mg, 0.38 mmol) and 2-mercaptobenzoic acid (118 mg, 0.77 mmol) were added to 5 ml of trifluoroacetic acid at RT. The mixture was stirred as a slurry at RT under an atmosphere of nitrogen over night. 2M NaOH and EtAc were added and the phases were separated. The solvents were evaporated and the residue was purified by flash chromatography with heptane/EtAc 4:1 as eluent to provide 4-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole in 86% yield. ES/MS m/z: 319.1 (M+H)

Workup

  1. customthe phases were separated
  2. customThe solvents were evaporated
  3. customthe residue was purified by flash chromatography with heptane/EtAc 4:1 as eluent

Sources & evidence

ORD record
ord-519f5bc359864b18afbc0a04024d84b0
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

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