Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Cyanophenylboronic acid | HCID 2734610 | — |
| Reactant | 1-Boc-1-methylhydrazine | HCID 3748280 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 57941326 | HCID 57941326 | 29.3% |
Reaction Steps
A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 890 mg, 6.06 mmol), 2-cyanophenylboronic acid (CombiBlock; 1.00 g, 6.8 mmol), copper(II) acetate (1.25 g, 6.9 mmol) and triethylamine (2 mL, 14.4 mmol) in 1,2-dichloroethane (30 mL) was heated in an oil bath at 60° 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 10-20% ethyl acetate/hexanes, to give N′-(2-cyano-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (439 mg, 29%) as a pale yellow 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-b174a210561f4ae5a886f0747e85f5cd |
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| Source note | uspto-grants-2009_11 |
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