HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Methyl 3-{[[(3-bromo-4-fluorophenyl)methyl](methyl)amino]carbonyl}benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Methoxycarbonyl)benzoic acid | HCID 601880 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | [(3-Bromo-4-fluorophenyl)methyl](methyl)amine | HCID 16781426 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 3-{[[(3-bromo-4-fluorophenyl)methyl](methyl)amino]carbonyl}benzoate | HCID 57813368 | 68% |
Reaction Steps
To a solution of [(3-bromo-4-fluorophenyl)methyl]methylamine (0.355 g, 1.63 mmol) in THF (16 mL) was added 3-[(methyloxy)carbonyl]benzoic acid (0.294 g, 1.63 mmol), HBTU (0.929 g, 2.45 mmol), Et3N (0.458 mL, 3.26 mmol) and stirred at room temperature for 65 h, and then quenched with H2O. The organic layer was loaded onto silica gel cartridge and purified by CombiFlash chromatograph to afford the title compound 0.419 g (68%). LC-MS m/z 380 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08067408B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-8ae4e70cfc124837a350a017d30c2134 |
| Source note | uspto-grants-2011_11 |