Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,5-bis(trifluoromethyl)phenylboronic acid | HCID 2779084 | — |
| Reactant | 1-Boc-1-methylhydrazine | HCID 3748280 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 57941520 | HCID 57941520 | 39.4% |
Reaction Steps
A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 600 mg, 3.4 mmol), 2,5-bis(trifluoromethyl)phenylboronic acid (ChemFocus, LLC, East Brunswick, N.J., USA; 953 mg, 3.7 mmol), copper(II) acetate (746 mg, 4.1 mmol) and triethylamine (575 μL, 4.1 mmol) in 1,2-dichloroethane (18 mL) was heated in an oil bath at 50° C. for 2 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 10% ethyl acetate/hexanes, to give N′-(2,5-bis-trifluoromethyl-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (480 mg, 33%) as a colorless oil that solidified.
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-a38f2d0390bc48a7afaac4c40a334e2b |
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| Source note | uspto-grants-2009_11 |
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