Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | (2-Amino-4-(methoxycarbonyl)phenyl)boronic acid | HCID 2737801 | — |
| Reactant | Ethyl 3-bromoisonicotinate | HCID 15141565 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 50942139 | HCID 50942139 | 55.7% |
Reaction Steps
Ethyl 3-bromoisonicotinate (1.15 g, 5.0 mmol), 2-amino-4-(methoxycarbonyl)phenylboronic acid (1.04 g, 4.5 mmol), sodium acetate (1.64 g, 20 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (complexed with dichloromethane), (182 mg, 0.25 mmol) and dimethylformamide (7.5 mL) were combined in a flask. The flask was evacuated and filled with nitrogen twice and heated to 125° C. with stirring for 12 hours or until LCMS indicated the absence of any starting material. The mixture was cooled to room temperature and water (100 mL) was added to form a brown precipitate. The precipitate was filtered to yield 637 mg of methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carboxylate. LCMS (ESI) 255.4 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08853235B2 |
|---|
| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-b4471b2d5ffa48459d939217875144df |
|---|
| Source note | uspto-grants-2014_10 |
|---|
