Abstract
A practical modification of the Gassman 3-(methylthio)oxindole synthesis is reported. In our method, substituted anilines and 2-(methylthio)acetamide were reacted under mild reaction conditions, in the presence of N-chlorophthalimide as a chlorinating agent to give α-amidosulfides, which, in the next step of the process, were cyclized to give 3-(methylthio)oxindoles. The method was successfully applied for the synthesis of the key intermediate, 2-(2-amino-3-benzoylphenyl)-2-(methylthio)acetamide, in the process of the preparation of nepafenac, a commonly used ophthalmic drug.
Original language | English (US) |
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Pages (from-to) | 5423-5425 |
Number of pages | 3 |
Journal | Tetrahedron Letters |
Volume | 55 |
Issue number | 40 |
DOIs | |
State | Published - Oct 1 2014 |
Keywords
- 3-(Methylthio)oxindoles
- Gassman reaction
- N-Chlorophthalimide
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry