Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Borono-3-methoxybenzoic acid | HCID 23134276 | — |
| Reactant | 6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine | HCID 86710539 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86710556 | HCID 86710556 | — |
Reaction Steps
To a microwave vial was added 6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (Intermediate 1-1, 100 mg, 0.35 mmol), 4-borono-3-methoxybenzoic acid (76 mg, 0.39 mmol), PdCl2(dppf).CH2Cl2 (29 mg, 0.035 mmol), Na2CO3 (112 mg, 1.06 mmol), DMF (2 mL) and water (0.5 mL). The microwave vial was sealed and heated in a microwave at 120° C. for 45 min. The crude reaction mixture was cooled and diluted in water and ether. The aqueous layer was extracted with ether. The resultant emulsion was diluted in water and 1 M NaOH. The aqueous layer was acidified with 1 M HCl slowly and extracted again with ether. The organic layer was concentrated under reduced pressure, and the resulting precipitate was suspended in 10 mL MeOH and filtered. The filtrate was concentrated and used without further purification. LCMS Rt=0.63 min (condition B); MS (M+1)=399.0
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08729263B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-667e7c1fe362406597737c664f7e9bb2 |
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| Source note | uspto-grants-2014_05 |
|---|
