Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(4-BOC-Piperazino)phenylboronic acid | HCID 5233014 | — |
| Reactant | HCID 86594551 | HCID 86594551 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86594552 | HCID 86594552 | — |
Reaction Steps
To (2S)-2-(4-bromoanilino)-N-(cyanomethyl)-4-methylpentanamide (555 mg, 1.71 mmol), and 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (520 mg, 1.71 mmol) in DMF (20 mL) under dry nitrogen was added aqueous sodium carbonate (2 M, 2.55 mL, 5.13 mmol) followed by the catalyst PdCl2(dppf) (42 mg, 0.051 mmol). The reaction was heated to 105° C. for 0.75 hours and more PdCl2(dppf) (42 mg, 0.051 mmol) was added and the reaction mixture was heated for another 4–5 hours. Water was added and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6 then 1/1) to afford tert-butyl 4-{4′-[((1S)-1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino][1,1′-biphenyl]-4-yl}-1-piperazinecarboxylate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07012075B2 |
|---|
| Source dataset | uspto-grants-2006_03 |
|---|
| ORD ID | ord-6ab4f7a2e247469782745b72b4549539 |
|---|
| Source note | uspto-grants-2006_03 |
|---|
