1,1'-Carbonyldiimidazole → N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-(phenylethynyl)nicotinamide

HRID 391510

Reaktionsgleichung

[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=2)[C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:30][S@:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[NH:33])=[O:32]>C1COCC1>[CH3:30][S:31](=[O:32])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[N:33][C:14](=[O:16])[C:13]1[CH:17]=[C:9]([C:8]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:10]=[N:11][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a slurry of 5-(2-phenyleth-1-ynyl)nicotinic acid (339 mg, 1.5 mmol) in 6.0 mL THF at room temperature was added 1,1′-carbonyldiimidazole (271 mg, 1.7 mmol). After stirring 1.25 hour, a solution of (S)-(+)-S-methyl-S-phenylsulfoximine (260 mg, 1.7 mmol) in 1.5 mL THF was added and the mixture heated at 50° C. for 22 hours. Then an additional 50 mg (0.32 mmol) (S)-(+)-S-methyl-S-phenylsulfoximine was added and heating continued at 60° C. for 3.5 hours. The reaction was quenched with NaHCO3 solution and then extracted into EtOAc. The EtOAc layer was washed with NaHCO3 solution, H2O, brine, dried with anhydrous Na2SO4 and concentrated. The yellow oil obtained was chromatographed eluting with hexane/EtOAc to give N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-(phenylethynyl)nicotinamide as a white foam (303 mg, 55%).

Aufarbeitung

temperatureheating
waitcontinued at 60° C. for 3.5 hours
customThe reaction was quenched with NaHCO3 solution
extractionextracted into EtOAc
washThe EtOAc layer was washed with NaHCO3 solution, H2O, brine
dry with materialdried with anhydrous Na2SO4
concentrationconcentrated
customThe yellow oil obtained
customwas chromatographed
washeluting with hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-b6735c799eee440db8eae84f1f4af96f
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08383825B2

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