Methanol → 6-Chloro-2-(3-methoxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole

HRID 2190778Notes

Reaction equation

[Cl:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3F)[O:8][C:4]=2[CH:3]=1.[C:22](=O)([O-])[O-:23].[K+].[K+].CO>O>[Cl:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[O:23][CH3:22])[O:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.28 g of 6-chloro-2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.24 g of potassium carbonate and 3 ml of methanol was stirred while heating at 60° C. for two hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.13 g of 6-chloro-2-(3-methoxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 91”).

Workup

extractionfollowed by extraction with ethyl acetate twice
washThe combined organic layers were washed with a saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5ec58000f0f645a2b3ce6bcd0d002e08
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324387B2

Reaction notes

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