Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methyl 4-aminothiophene-3-carboxylate | HCID 2777610 | — |
| Reactant | HCID 86654952 | HCID 86654952 | — |
| Solvent | (Trifluoromethyl)benzene | HCID 7368 | — |
| Product | HCID 67308959 | HCID 67308959 | 74.6% |
Reaction Steps
To a solution of 1-benzyloxycarbonyl-3-isocyanato-5-trifluoromethylindole-2-carboxylic acid tert-butyl ester 5E (˜4.10 mmol) in trifluoromethylbenzene (10 mL) was added 4-aminothiophene-3-carboxylic acid methyl ester 5F (1.30 g, 8.28 mmol). The reaction mixture was heated in a microwave reactor at 150° C. for 30 minutes. Ethyl acetate (100 mL) was added and the organic layer was washed with 1 N hydrochloric acid and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to provide 1-benzyloxycarbonyl-3-[3-(4-methoxycarbonylthiophen-3-yl)-ureido]-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 5G (1.89 g, 3.06 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765757B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-84ea3e4103024845ac82a6a921d0cbc5 |
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| Source note | uspto-grants-2014_07 |
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