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Potassium Phosphate, Tribasic → 3-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile

HRID 1467387
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1467387
FC(F)(F)S(O[C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:14]2[N:13]=[CH:12][C:11]3[N:19]([CH3:32])[C:20](=[O:31])[N:21]([C:22]4[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:23]=4[F:30])[C:10]=3[C:9]=2[CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB(/[CH:43]=[CH:44]/[C:45]2[CH:49]=[CH:48][S:47][CH:46]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O=O>[F:30][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:22]=1[N:21]1[C:10]2[C:9]3[CH:8]=[C:7](/[CH:43]=[CH:44]/[C:45]4[CH:49]=[CH:48][S:47][CH:46]=4)[C:16]([O:17][CH3:18])=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:19]([CH3:32])[C:20]1=[O:31])[C:28]#[N:29]
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Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 162183494,4,5,5-Tetramethyl-2-[(E)-2-(thiophen-3-yl)ethenyl]-1,3,2-dioxaborolaneHCID 866891791-(4-Cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl trifluoromethanesulfonate

Produkt 1

HCID 568476433-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile
Ausbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 977OxygenLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

1-(4-Cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl trifluoromethanesulfonate (119 mg, 240 μmol), 4,4,5,5-tetramethyl-2-[(E)-2-thiophen-3-ylvinyl]-1,3,2-dioxaborolane (142 mg, 602 μmol), tripotassium phosphate (107 mg, 504 μmol) and trans-bis(tricyclohexylphosphine)palladium(II) dichloride (18 mg, 24 μmol) were dissolved in oxygen-free N,N-dimethylformamide (5 ml). The mixture was subsequently heated at 130° C. for 45 min (microwave). The reaction mixture was then filtered with suction, the filtrate was diluted with water and stirred at room temperature for 30 min. The precipitate formed was filtered off with suction and rinsed with water. The residue was chromatographed on flash silica gel (solvent gradient ethyl acetate/0-25% by vol. of ethanol), giving 3-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile (90 mg, 181 μmol) as solid. MS: 457.1 (M+H+), TLC (HPTLC): Rf=0.47 (ethyl acetate/ethanol 2:1, parts by volume).

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered with suction
  2. additionthe filtrate was diluted with water
  3. customThe precipitate formed
  4. filtrationwas filtered off with suction
  5. washrinsed with water
  6. customThe residue was chromatographed on flash silica gel (solvent gradient ethyl acetate/0-25% by vol. of ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-048283d548bf4cf7954bf1730f8d78bd
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000153B2

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