Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Amino-3-chlorobenzonitrile | HCID 12627363 | — |
| Reactant | 4-Azido-5-fluoropyridine-3-carbaldehyde | HCID 86697053 | — |
| Catalyst | Titanium Tetrachloride | HCID 24193 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178509759 | HCID 178509759 | — |
Reaction Steps
A solution of 4-azido-5-fluoropyridine-3-carbaldehyde (2.86 g, 17.2 mmol) and 2-amino-3-chlorobenzonitrile (2.62 g, 17.2 mmol) in DCM (60 mL) was cooled to 0° C. under an atmosphere of nitrogen. Triethylamine (7.2 mL, 51.6 mmol) was added, followed by dropwise additiona of titanium (IV) chloride solution (1 N in DCM, 10.3 mL, 10.3 mmol). The reaction mixture was stirred at 0° C. for 2 hours, then at room temperature overnight. The resultant mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure and the residue obtained was used in the following step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09309240B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-747c075dda2142859ccab31f8fcf30c5 |
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| Source note | uspto-grants-2016_04 |
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