HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → (E)-3-{3-[6-(4-Methyl-[1,4]diazepan-1-yl)pyrazin-2-yl]-phenyl}-acrylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Methyl (2E)-3-(3-boronophenyl)-2-propenoate | HCID 5708388 | — |
| Reactant | 1-(6-Chloropyrazin-2-yl)-4-methyl-1,4-diazepane | HCID 47137467 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (E)-3-{3-[6-(4-Methyl-[1,4]diazepan-1-yl)pyrazin-2-yl]-phenyl}-acrylic acid methyl ester | HCID 24812011 | 61.7% |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
[3-(E-3-methoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid (125 mg, 0.61 mmol) and bistriphenylphosphinepalladium(II)chloride (30 mg, 0.057 mmol) were combined in a microwave reaction tube. Subsequently 1-(6-chloro-pyrazin-2-yl)-4-methyl-[1,4]diazepane (130 mg, 0.57 mmol) was added as a solution in DMF (8 mL) followed by an aqueous solution of Na2CO3 (2M, 3 mL, 6 mmol). The tube was sealed and the reaction mixture was heated in the microwave at 120° C. for 20 min. The reaction mixture was then filtered through a plug of celite, and purified by flash chromatography to provide the title compound (124 mg 61%); MS analysis electrospray, 353 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08318723B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-1576edcf610c48b5b363f6244c212689 |
| Source note | uspto-grants-2012_11 |