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

HRID 383461ノート

反応式

HRID 383461 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-519f5bc359864b18afbc0a04024d84b0
出典データセット
uspto-grants-2013_02
特許番号
US08367665B2

反応ノート

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