Citric Acid → (2-Amino-5-bromo-3-pyridyl)-phenylketone

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Reaktionsgleichung

Cl.CON(C)[C:5](=[O:14])[C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[N:8][C:7]=1[NH2:13].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>C1COCC1.CCOCC>[NH2:13][C:7]1[C:6]([C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])=[CH:11][C:10]([Br:12])=[CH:9][N:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: -50 °C

Versuchsvorschrift

1.00 g (3.38 mmol) of N-methoxy-N-methyl-2-amino-5-bromonicotinamide hydrochloride was suspended in 50 ml of anhydrous THF under nitrogen. The suspension was cooled to −50° C. and 13.5 ml of a 1.0 M solution of phenylmagnesium bromide in ether was added rapidly to afford an orange solution. The mixture was stirred, and slowly warmed to room temperature. The resulting yellow-orange solution was distributed between 75 ml of a 10% aqueous citric acid solution and 200 ml of ethyl acetate. The organic phase was separated and washed with 75 ml of a 10% aqueous citric acid solution and 75 ml of saturated aqueous sodium bicarbonate solution. The organic phase was then dried over sodium sulfate and evaporated to afford 985 mg of a yellow crystalline solid. 1H-NMR (d6-DMSO) δ: 8.34 [1H] d, 7.72 [2H] s, 7.70 [1H] d, 7.65 [1H] t(m), 7.63 [2H] d(m), 7.56 [2H] t(m). MS: m/z 277 [MH+].

Aufarbeitung

customto afford an orange solution
temperatureslowly warmed to room temperature
customThe organic phase was separated
washwashed with 75 ml of a 10% aqueous citric acid solution and 75 ml of saturated aqueous sodium bicarbonate solution
dry with materialThe organic phase was then dried over sodium sulfate
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-d5ba927e31134efe9f3a843a11b7e2e4
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07582637B2

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