3-Nitrophthalic anhydride → (Z)-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)-4-nitroisobenzofuran-1(3H)-one

HRID 1091726

Reaktionsgleichung

Reaktionsgleichung von HRID 1091726
C([O-])(=O)C.[Na+].[N+:6]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=O)[O:12][C:13]2=[O:18])([O-:8])=[O:7].[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]C(O)=O)=[CH:23][C:22]=1[C:31]([N:33]1[CH2:38][CH2:37][CH:36]([O:39][CH3:40])[CH2:35][CH2:34]1)=[O:32]>>[F:20][C:21]1[CH:26]=[CH:25][C:24](/[CH:27]=[C:11]2\[O:12][C:13](=[O:18])[C:14]3[C:10]\2=[C:9]([N+:6]([O-:8])=[O:7])[CH:17]=[CH:16][CH:15]=3)=[CH:23][C:22]=1[C:31]([N:33]1[CH2:34][CH2:35][CH:36]([O:39][CH3:40])[CH2:37][CH2:38]1)=[O:32]

Komponenten

4

Edukt 3

HCID 216313-Nitrophthalic anhydrideHCID 517045Sodium AcetateHCID 577917632-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic Acid

Produkt 1

HCID 57791796(Z)-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)-4-nitroisobenzofuran-1(3H)-oneAusbeute 6,9 %

Reaktionsbedingungen

Temperatur
240 °C

Versuchsvorschrift

Sodium acetate (6.97 mg, 0.08 mmol) was added to 4-nitroisobenzofuran-1,3-dione (558 mg, 2.89 mmol) and 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic acid (43) (502 mg, 1.70 mmol) under air. The resulting mixture was stirred at 240° C. for 30 minutes. The cooled mixture was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the desired material as a yellow gum (50 mg, 6.90% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.59-2.00 (4H, m), 3.10-3.26 (1H, m), 3.37 (3H, s), 3.43-3.57 (2H, m), 3.61-3.71 (1H, m), 3.88-4.05 (1H, m), 7.16-7.20 (1H, m), 7.30 (1H, s), 7.70-7.76 (1H, m), 7.86-7.88 (1H, m), 7.97-8.01 (1H, m), 8.27 (1H, d), 8.39 (1H, d); m/z (LC-MS, ESI+), RT=2.29 (M+H 427.3).

Aufarbeitung

  1. customThe cooled mixture was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane
  2. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4d2ba946f5a44fe192c4be30cc6d3cce
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129380B2

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