HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 2-fluoro-4-methoxy-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline | HCID 821084 | — |
| Reactant | 2-Fluoro-4-methoxybenzoic acid | HCID 2774542 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Thionyl Chloride | HCID 24386 | — |
| Product | 2-fluoro-4-methoxy-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide | HCID 58341977 | 80% |
Reaction Steps
A stirred solution of 2-fluoro-4-methoxybenzoic acid (0.23 g, 1.34 mmol) in thionyl chloride (7 ml) containing a drop of DMF was heated under reflux for 4 h. The excess reagent was then removed under reduced pressure to give a crude solid. The amide was prepared as described in the Amide Coupling section using the crude solid and 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (0.30 g, 1.34 mmol) in dry pyridine (15 ml) to give the title compound (0.323 g, 80%) as a colourless solid after work-up and flash chromatography (EtOAc).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895313B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-3fd8ef6692d0443481f0906cd83965d0 |
| Source note | uspto-grants-2014_11 |