Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | trans-2-(4-Fluorophenyl)vinylboronic acid | HCID 5706776 | — |
| Reactant | 2-(5-Bromo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide | HCID 59489539 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethyl Ether | HCID 8254 | — |
| Product | HCID 68493006 | HCID 68493006 | 64.5% |
Reaction Steps
Part A. To a solution of 2-(5-bromo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (35 mg, 0.09 mmol, 1.0 equiv) in dimethyl ether (1 mL) was added, Na2CO3 (19 mg, 0.18 mmol, 2.0 equiv), trans-2-(4-fluorophenyl)vinyl boronic acid (37 mg, 0.22 mmol, 2.5 equiv), PdCl2(dppf) (3.0 mg, 5 mol %) and water (0.1 mL) in a sealed tube. The reaction was heated in microwave oven at 100° C. for 1 hr. The reaction mixture was cooled and the solvent was removed in vacuo. The crude product was purified by column chromatography [SiO2, methanol/dichloromethane, 0:100 to 15:85, v/v] to afford 2-{5-[(E)-2-(4-fluoro-phenyl)-vinyl]-pyrazin-2-yl}-4-methyl-thiazole-5-carboxylic acid benzylamide (25 mg, 64%). MS (M+H)+=431.1, Rt=1.66 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08314138B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-ab5ffaa9a93742a5bb4ccb669c42e4eb |
|---|
| Source note | uspto-grants-2012_11 |
|---|
