Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | HCID 18466610 | HCID 18466610 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 18466618 | HCID 18466618 | 33.2% |
Reaction Steps
A solution of 5-bromo-2-(cyclopropylamino)-N-(2,6-dichloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide (105 mg, 0.254 mmol) in pyridine (3.0 mL) was heated to 50° C. while a 1 M solution of NaHMDS in THF (0.53 mL, 0.53 mmol) was added. The resulting solution was stirred at 50° C. for 3 h. The reaction was quenched with aqueous saturated NH4Cl, diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified via flash chromatography (hexane:EtOAc, 7:3) to give the title compound (32 mg, 33% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06420359B1 |
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| Source dataset | uspto-grants-2002_07 |
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| ORD ID | ord-7ae15e5a6c0549a1989c3e53a748f19b |
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| Source note | uspto-grants-2002_07 |
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