Potassium Carbonate → Methyl 5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoate

HRID 2080676Notes

Reaction equation

[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:21]1[CH:22]=[CH:23][C:24]([N+:31]([O-:33])=[O:32])=[C:25]([CH:30]=1)[C:26]([O:28][CH3:29])=[O:27].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:21]3[CH:22]=[CH:23][C:24]([N+:31]([O-:33])=[O:32])=[C:25]([CH:30]=3)[C:26]([O:28][CH3:29])=[O:27])=[CH:9][CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.54 g of 6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-ol and 1.86 g of potassium carbonate were added to a dimethylformamide (10 ml) solution of 955 mg of methyl 5-fluoro-2-nitrobenzoate, and stirred at 80° C. for 1 hour. This was restored to room temperature, then aqueous saturated ammonium chloride solution was added to it, extracted with ethyl acetate, and the organic layer was dried, and the solvent was evaporated away under reduced pressure to obtain 1.38 g of methyl 5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoate as a yellow solid.

Workup

customThis was restored to room temperature
extractionextracted with ethyl acetate
customthe organic layer was dried
customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record: ord-625af5e286ec40b0a537fb80ddf59b31
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932394B2

Reaction notes

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