Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Pyridinecarboxaldehyde | HCID 10371 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | 4,6-dichloro-3-phenylpyridazine | HCID 2736076 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86717327 | HCID 86717327 | 123.4% |
Reaction Steps
To a solution of 4,6-dichloro-3-phenyl-pyridazine (2.27 g, 0.01 mol) in dry THF (30 mL) was added pyridine-3-carbaldehyde (1.3 g, 0.012 mol). The reaction mixture was cooled down to −78° C. and a solution of LDA (2 N, 22 mL) was added dropwise, keeping the internal temperature below −50° C. The reaction mixture was stirred for 3 h, then water and ethyl acetate were added. Phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried (phase separator cartridge) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 9:1 to 8:2) yielding the title compound as a solid (4.1 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09227976B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-5a0615ea84e347349d0ac9fe810c68f5 |
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| Source note | uspto-grants-2016_01 |
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