Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine | HCID 17750486 | — |
| Reactant | 2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide | HCID 57959396 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethyl Ether | HCID 8254 | — |
| Product | HCID 24954330 | HCID 24954330 | 23.1% |
Reaction Steps
Part B. To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid benzylamide (350 mg, 1.13 mmol, 1.0 equiv) in dimethyl ether (4 mL) was added Na2CO3 (240 mg, 2.26 mmol, 2.0 equiv), 6-chloropyrazine-2-boronic acid pinacol ester (680 mg, 2.82 mmol, 2.5 equiv), PdCl2(dppf) (83 mg, 0.11 mmol, 0.1 equiv) and water (1 mL) in a sealed tube. The reaction was immersed in an oil bath preheated to 50° C. After 3 days, the reaction was cooled and the solvent was removed in vacuo. The crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to give 2-(6-chloropyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (90 mg, 23% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.27 (s, 1H), 8.93 (s, 1H), 7.31-7.39 (m, 4H), 7.23-7.30 (m, 1H), 4.46 (d, J=8.0 Hz, 2H), 2.67 (s, 3H); MS (M+H)+=345.1, Rt=1.46 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08314138B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-2a958f1d03634b57a6ff64943905d3fa |
|---|
| Source note | uspto-grants-2012_11 |
|---|
