Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (2,3-Difluorophenyl)boronic acid | HCID 2734333 | — |
| Reactant | 1-Boc-1-methylhydrazine | HCID 3748280 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 57941323 | HCID 57941323 | 52% |
Reaction Steps
A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 500 mg, 3.4 mmol), 2,3-difluorophenylboronic acid (Aldrich; 529 mg, 3.35 mmol), copper(II) acetate (621 mg, 3.4 mmol) and triethylamine (480 μL, 3.4 mmol) in 1,2-dichloroethane (4 mL) was heated in an oil bath at 50° C. for 3 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 40 g column, eluting with 20-40% ethyl acetate/hexanes, to give N′-(2,3-difluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (450 mg, 39%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07622492B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-07ebcacacc89460e9cd5c5702e7ea948 |
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| Source note | uspto-grants-2009_11 |
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