Diethyl Ether → HCID 22677378, compound

HRID 1837461Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=1[Cl:16])(=[O:3])[CH3:2].[CH2:17]([O:19][CH:20]=[CH:21][Sn](CCCC)(CCCC)CCCC)[CH3:18].[F-].[Cs+].CCOCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[CH2:18])[N:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=1[Cl:16])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of methyl 4-acetamido-3,6-dichloropyridine-2-carboxylate (0.988 g, 4.0 mmol), ethoxyvinyltributyltin (2.70 mL, 8.0 mmol) and cesium fluoride (1.34 g, 8.8 mmol) in dioxane (20 mL) was sparged with nitrogen for 15 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.140 g, 0.2 mmol) was then added and the mixture was heated at 100° C. for 5 hours. After cooling, ether was added and the reaction mixture filtered through a silica plug. The solvents were removed and the crude product was purified by chromatography (ethyl acetate:hexane (1:2)) to give methyl 4-acetamido-3-chloro-6-(1-ethoxyvinyl)pryidine-2-carboxylate (0.780 g, 2.6 mmol). 1H NMR (CDCl3): δ 8.85 (s, 1H), 7.90 (br.s, 1H), 5.47 (d, J=2.0 Hz, 1H), 4.44 (d, J=2.0 Hz, 1H), 4.01 (s, 3H), 3.98 (q, J=7.0 Hz, 2H), 2.32 (s, 3H), 1.46 (t, J=7.0 Hz, 3H).

Workup

temperatureAfter cooling
filtrationthe reaction mixture filtered through a silica plug
customThe solvents were removed
customthe crude product was purified by chromatography (ethyl acetate:hexane (1:2))

Sources & evidence

ORD record: ord-6be4022312594b01a6726b1e8330fdee
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06784137B2

Reaction notes

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