HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)aniline → methyl 8-(4-amino-2,5-difluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)aniline | HCID 57955144 | — |
| Reactant | Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate | HCID 86696543 | — |
| Product | methyl 8-(4-amino-2,5-difluoro-phenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | HCID 86696568 | 76.1% |
Reaction Steps
Methyl 8-(4-amino-2,5-difluoro-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 (500 mg, 1.71 mmol) and 2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-aniline (667 mg, 2.06 mmol). Purification by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (500 mg, 75%). ESI-MS m/z: 407 (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08962842B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-dffb590c40a4498489112c318a86970e |
| Source note | uspto-grants-2015_02 |