HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 3'-(4-Ethoxyphenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Ethoxyphenylboronic acid | HCID 2734351 | — |
| Reactant | Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate | HCID 11150691 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3'-(4-Ethoxyphenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl ester | HCID 68738789 | 191.6% |
Reaction Steps
Couple 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (0.726 g, 2.43 mmol) and 4-ethoxyphenylboronic acid (0.95 g, 5.991 mmol), in the presence of triphenylphosphine (0.202 g, 0.770 mmol), palladium acetate (0.056 g, 0.243 mmol), sodium carbonate (3.8 mL of a 2 N solution in water) in a mixture of acetonitrile (42 mL) and water (8 mL). Reflux for 3 hr. Purify by silica gel chromatography, eluting with 0:100 to 25:75 ethyl acetate:hexanes, to give 3′-(4-ethoxyphenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (1.79 g, 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08202873B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-a29f0350fe5143cda44a4d28bc914b64 |
| Source note | uspto-grants-2012_06 |