Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methoxyacetyl chloride | HCID 96623 | — |
| Reactant | 6-Amino-5-fluoroindolin-2-one | HCID 10103504 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67530877 | HCID 67530877 | 40.9% |
Reaction Steps
5-Fluoro-6-Amino-indol-2-one 9d (2.028 g, 12.2 mmol) was dissolved in 30 mL of tetrahydrofuran under stirring at room temperature, and 1.3 mL of pyridine was then added to the solution. The reaction system was cooled down to −50° C. in a dry ice-ethanol bath. Methoxy-acetyl chloride (1.35 g, 12.5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring, and the solution was then added dropwise to the above reaction system. Upon completion of the addition, the dry ice-ethanol bath was removed. The reaction system was allowed to warm up to room temperature and stirred overnight until TLC showed the disappearance of starting materials. The resulting solid was filtered, washed with water (10 mL ×3) and recrystallized from methanol to give the title compound 5-fluoro-6-methoxyacetamido-2-oxoindole 13a (1.18 g, yield 40.6%) as a gray solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08299069B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-54bb86e3c1714a44b3db0e098e5df4dd |
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| Source note | uspto-grants-2012_10 |
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