Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,6-Dichloro-4-fluoroaniline | HCID 2774008 | — |
| Reactant | 4-Azido-5-fluoropyridine-3-carbaldehyde | HCID 86697053 | — |
| Catalyst | Titanium Tetrachloride | HCID 24193 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178514519 | HCID 178514519 | — |
Reaction Steps
To a cooled (0° C.) solution of 4-azido-5-fluoro-pyridine-3-carbaldehyde (2.44 g, 14.7 mmol), 2,6-dichloro-4-fluorophenylamine (2.65 g, 14.7 mmol) and triethylamine (6.1 mL, 44 mmol) in DCM (50 mL) was added titanium tetrachloride (1M in DCM, 8.8 mL, 8.8 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 hour, warmed to room temperature, and stirred for a further 4 hours. The mixture was concentrated under reduced pressure. The residue was dissolved in toluene and filtered through Celite®. The filtrate was concentrated under to dryness under reduced pressure to afford the title compound that was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09309240B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-da6f08ddb3384eeab3f246e0db6b358c |
|---|
| Source note | uspto-grants-2016_04 |
|---|