HuagongsheHuagongshe Chemistry Print Report · For research reference only
Citric Acid → HCID 86619566, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Amino-3,5-dibromopyrazine | HCID 620004 | — |
| Reactant | 2-Chlorophenylboronic acid | HCID 2734322 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 86619566 | HCID 86619566 | 54% |
Reaction Steps
Tetrakis(triphenylphosphine)palladium (0.24 g) is added at room temperature to a solution of 2-amino-3,5-dibromopyrazine (0.51 g) in dimethoxyethane (12 mL). The mixture is stirred for 30 min and sodium carbonate (0.53 g), water (6 mL) and 2-chlorophenylboronic acid (0.32 g) are added and the mixture is stirred for 18 h at 100° C. The mixture is cooled, citric acid (10%, 20 mL) is added and the mixture is extracted with ethyl acetate (3×50 mL). Organic phases were pooled, washed with sodium bicarbonate and brine, dried with Na2SO4 and the solvent was evaporated. The residue was purified by chromatography on silica gel with dichloromethane to yield 0.31 g of the title compound as a white solid, mp 138.5-139.5° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08188093B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-93f4dd944ffe48d8a0b894fbe5847d0e |
| Source note | uspto-grants-2012_05 |