Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(4-BOC-Piperazino)phenylboronic acid | HCID 5233014 | — |
| Reactant | 4-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]leucinate | HCID 69151763 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69151040 | HCID 69151040 | — |
Reaction Steps
To 4-methoxybenzyl N-[4-bromo-1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]leucinate (1.45 g, 2.92 mmol), 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (1.117 g, 3.65 mmol, prepared as described in Example 1) and catalyst PdCl2(dppf) (75 mg, 0.09 mmol) in DMF (30 mL) under dry nitrogen was added aqueous sodium carbonate (2.0 M, 3.3 mL, 6.6 mmol). The reaction was heated to 90° C. for 0.5 hour and an additional aliquot of PdCl2(dppf) (20 mg, 0.022 mmol) was added and the reaction mixture was heated for 1½ hour. 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, 25/75) to afford 4-methoxybenzyl N-(1-(tert-butoxycarbonyl)-4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucinate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07012075B2 |
|---|
| Source dataset | uspto-grants-2006_03 |
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| ORD ID | ord-c849a78007c04c7eb8f4859a470a08a7 |
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| Source note | uspto-grants-2006_03 |
|---|
