4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide → 1-(4-(5-Fluoropyridin-2-yl)phenyl)ethanone

HRID 216324Notes

Reaction equation

[CH3:1][Mg]Br.[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:22]=[CH:21][C:14]([C:15](N(OC)C)=[O:16])=[CH:13][CH:12]=2)=[N:9][CH:10]=1>O1CCCC1>[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:22]=[CH:21][C:14]([C:15](=[O:16])[CH3:1])=[CH:13][CH:12]=2)=[N:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methylmagnesium bromide (3 M in tetrahydrofuran) (2.1 mL, 6.2 mmol) was added to a −78° C. solution of 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide (800 mg, 3.1 mmol) in tetrahydrofuran (20 mL). After stirring at 0° C. for 30 min, the reaction mixture was quenched with methanol and saturated aqueous ammonium chloride. The organic layer was dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-15% ethyl acetate/hexane afforded the title compound.

Workup

customthe reaction mixture was quenched with methanol and saturated aqueous ammonium chloride
dry with materialThe organic layer was dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fb6eadfff345482abeb6415983a5f2e8
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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