Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | HCID 69457730 | HCID 69457730 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59026806 | HCID 59026806 | 40.9% |
Reaction Steps
To a solution of {N′-[3-(2-Fluoro-4-iodo-phenylamino)-pyridine-4-carbonyl]-hydrazino}-oxo-acetic acid ethyl ester (1.27 g, 2.69 mmol, 1.0 eq.) in DCM (20 mL) containing pyridine (0.55 g, 6.99 mmol. 2.66 eq.) thionyl dichloride (0.26 mL, 3.5 mmol; 1.30 eq) was added at 0° C. The reaction mixture were stirred at 0° C. for 2 hrs. The solvent was evaporated, toluene was added and the reaction mixture was stirred at 110° C. for 6 hrs. Removal of the solvent resulted in a residue that was subjected to silica gel column chromatography (EtOAc:Hex=1:2) to afford the desired product (0.50 g). [5.32 min; 455 (M+1)]
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08076486B2 |
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| Source dataset | uspto-grants-2011_12 |
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| ORD ID | ord-d20f5f4298cf4c5eb6cad6418093d308 |
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| Source note | uspto-grants-2011_12 |
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