2-Methylpyridine → 3-[(7-Methoxynaphthalen-2-yl)oxy]pyridin-2-amine

HRID 1622637Notes

Reaction equation

N1C=CC=CC=1C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24]([OH:28])=[CH:25]2)=[CH:20][CH:19]=1.Br[C:30]1[C:31]([NH2:36])=[N:32][CH:33]=[CH:34][CH:35]=1>[Cu]I.O.CS(C)=O>[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24]([O:28][C:30]3[C:31]([NH2:36])=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:25]2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of picoline acid (0.427 g), tripotassium phosphate (11.04 g), copper (I) iodide (0.660 g), 7-methoxynaphthalen-2-ol (6.04 g), 3-bromopyridin-2-amine (3 g) and DMSO (50 mL) was stirred under a nitrogen atmosphere at 140° C. overnight. Water was added, and the mixture was filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and basic silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.667 g) as a pale-yellow solid.

Workup

filtrationthe mixture was filtered through celite
extractionthe filtrate was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane) and basic silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-87580a9db6844132aed2c6c5d3b86432
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778934B2

Reaction notes

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