Methyl 6-chloropyridazine-3-carboxylate → HCID 89581292, compound

HRID 1501247Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([O:14][CH:15]=[CH:16][Sn])[CH3:13]>CN(C)C=O>[CH2:15]([O:14][C:12]([C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1)=[CH2:13])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of methyl 6-chloropyridazine-3-carboxylate (1.5 g, 8.7 mmol), ethoxyvinyl tin (3.2 g, 8.7 mmol), trans-bis(triphenyl-phosphine)palladium (200 mg) and N,N-dimethylformamide (50 mL) were combined. The mixture solution was heated to 80° C. for 10 hours under nitrogen gas protected. N,N-dimethylformamide was concentrated to dry in vacuo. The residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=4:1) to give methyl 6-(1-ethoxyvinyl)pyridazine-3-carboxylate as a white solid (1.3 g, 72%). 1H NMR (300 MHz, CDCl3): δ 8.22 (d, J=9 Hz, 1H), 7.98 (d, J=9 Hz, 1H), 4.98 (d, J=2.4 Hz, 1H), 4.68 (d, J=Methyl 6-acetylpyridazine-3-carboxylate. A solution of methyl 6-(1-ethoxyvinyl)pyridazine-3-carboxylate (1.3 g, 7.2 mmol) in hydrochloric acid (6 mol/L, 20 mL) was stirred at room temperature for 4 hours. The mixture solution was neutralized with potassium carbonate, extracted with ethyl acetate (100 mL). The organic layer was concentrated to dry to give methyl 6-acetylpyridazine-3-carboxylate as a white solid (0.9, 81%). 1H NMR (300 MHz, CDCl3): δ 8.36-8.40 (m, 1H), 8.36-8.40 (m, 1H), 4.00 (s, 3H), 2.82 (s, 3H).

Workup

concentrationN,N-dimethylformamide was concentrated
customto dry in vacuo
customThe residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=4:1)

Sources & evidence

ORD record: ord-b2f21467d42c4e1492b23af287f3d3f4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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