Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Boc-1-methylhydrazine | HCID 3748280 | — |
| Reactant | Biphenyl-2-boronic acid | HCID 4589187 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 57941381 | HCID 57941381 | 34.2% |
Reaction Steps
A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 1.46 g, 10.0 mmol), 2-biphenylboronic acid (Aldrich; 1.94 g, 10.0 mmol), copper(II) acetate (1.81 g, 10.0 mmol) and triethylamine (1.4 mL, 10.0 mmol) in 1,2-dichloroethane (10 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 5-40% ethyl acetate/hexanes, to give N′-biphenyl-2-yl-N-methyl-hydrazinecarboxylic acid tert-butyl ester (1.02 g, 34%) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07622492B2 |
|---|
| Source dataset | uspto-grants-2009_11 |
|---|
| ORD ID | ord-caaeb52195c64ff18aec8e246a8465a6 |
|---|
| Source note | uspto-grants-2009_11 |
|---|