Water → 6-Iodo-2-methoxypyridin-3-amine

HRID 70545Notes

Reaction equation

[I-:1].[Na+].CNCCNC.Br[C:10]1[N:15]=[C:14]([O:16][CH3:17])[C:13]([NH2:18])=[CH:12][CH:11]=1.O>O1CCOCC1.[Cu](I)I.C(OCC)(=O)C>[I:1][C:10]1[N:15]=[C:14]([O:16][CH3:17])[C:13]([NH2:18])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium iodide (40 g), copper iodide (6.0 g) and N,N′-dimethylethylenediamine (7 mL) was added to a solution of 6-bromo-2-methoxypyridin-3-amine (26 g) in 1,4-dioxane (250 mL) in a nitrogen gas stream, and the mixture was stirred at 120° C. for 14 hours. The reaction solution was left to cool, and then water and ethyl acetate were added. Filtration through celite was followed by extraction. The organic layer was washed with a 20% sodium thiosulfate solution and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15→70:30) to give 6-iodo-2-methoxypyridin-3-amine as a colorless powder (25 g, 75%).

Workup

waitThe reaction solution was left
temperatureto cool
filtrationFiltration through celite
extractionwas followed by extraction
washThe organic layer was washed with a 20% sodium thiosulfate solution and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15→70:30)

Sources & evidence

ORD record: ord-6669669f40b546e885aed106184607aa
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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