Ammonium Chloride → (6-chloropyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

HRID 626272

Reaktionsgleichung

I[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[CH:4][CH:3]=1.C([Li])CCC.[Cl:20][C:21]1[CH:32]=[CH:31][C:24]([C:25](N(OC)C)=[O:26])=[CH:23][N:22]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:20][C:21]1[N:22]=[CH:23][C:24]([C:25]([C:2]2[CH:14]=[CH:13][C:5]([O:6][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][O:8]3)=[CH:4][CH:3]=2)=[O:26])=[CH:31][CH:32]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

2-(4-Iodophenoxy)tetrahydro-2H-pyran (18.2 g, 59.9 mmol) was dissolved in 100 mL dry tetrahydrofuran and cooled to −78° C. under nitrogen atmosphere, and then n-butyllithium was added dropwise to the solution. After addition, the solution was stirred at −78° C. for 0.5 h, 6-chloro-N-methoxy-N-methylnicotinamide (8.0 g, 39.9 mmol) in 50 mL tetrahydrofuran was added dropwise and keep the temperature under −78° C. for 2 h. Then 100 mL of aqueous saturated ammonium chloride was added. The mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, concentrated in vacuo, and purified by column chromatography to give the desired product as a yellow solid (8.4 g, 66.3%).

Aufarbeitung

additionAfter addition
customunder −78° C.
customfor 2 h
extractionThe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-245bc76d81f1407194bb18726e7edb97
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09309211B2

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