HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → methyl 8-(4-amino-2-fluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 44755207 | — |
| Reactant | Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate | HCID 86696543 | — |
| Product | methyl 8-(4-amino-2-fluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | HCID 86696550 | 69.8% |
Reaction Steps
Methyl 8-(4-amino-2-fluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A using methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-aniline (122 mg, 0.51 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 94:6) afforded the title compound as a yellow solid (87 mg, 64%). ESI-MS m/z: 367 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08962842B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-12cc1cf3355f4780ab5ff37c5802253a |
| Source note | uspto-grants-2015_02 |