Share a compound : 55557-52-3

Some common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 55557-52-3

A.1.11. Synthesis of 3-aryl-pyrazine-2-carboxylic acids:; A.1.11.1 3-p-Tolyl-pyrazine-2-carboxylic acid; 3-Chloropyrazine-2-carbonitrile (3.0 g; 21.5 mmol) was dissolved in dimethoxyethane (65 ml) and 4-tolylboronic acid (3.2 g; 23.65 mmol) was added, followed by the addition of K2CO3 (8.2 g; 59 mmol) and water (30 ml). The reaction mixture was deoxygenized with N2 (g) for 3 minutes followed by the addition of triphenylphosphine (842 mg; 3.2 mmol) and palladium(II)acetate (237 mg; 1.06 mmol). The reaction mixture was heated to 900C for 14 h, cooled to rt, diluted with EtOAc, filtered over a plug of celite and dried with magnesiumsulfate. The organic solvent was evaporated under reduced pressure to give 5.3 g of S-p-tolyl-pyrazine-l-carbonitrile. The intermediate nitrile was dissolved in MeOH (110 ml) followed by the addition of 4M aq NaOH (180 ml). The resulting mixture was heated to 85C for 14 h, cooled to rt and the MeOH was evaporated under reduced pressure. The residual aq. phase was acidified to pH=2 by the addition of cone. HCl and the precipitated product was filtered off, dissolved in DCM / EtOAc and dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2.30 g of 3-p- tolyl-pyrazine-2-carboxylic acid. LC-MS: tR = 0.40 min; [M-H]+ = 213.14.

The chemical industry reduces the impact on the environment during synthesis 3-Chloropyrazine-2-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/104155; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem