Diisopropylamine → 6-(2-(4-chlorophenyl)-1,3-dioxolan-2-yl)-4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 1799174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799174
C(NC(C)C)(C)C.[Li]CCCC.[Li+].CC([N-]C(C)C)C.[C:21]([O:25]C(C)=O)(C)(C)[CH3:22].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2([C:41]3[CH:42]=[C:43]([C:49]([C:51]4[CH:56]=[CH:55][CH:54]=[C:53]([O:57][CH3:58])[CH:52]=4)=O)[C:44]([NH:47][CH3:48])=[N:45][CH:46]=3)[O:40][CH2:39][CH2:38][O:37]2)=[CH:32][CH:31]=1>C1COCC1>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2([C:41]3[CH:42]=[C:43]4[C:44](=[N:45][CH:46]=3)[N:47]([CH3:48])[C:21](=[O:25])[CH:22]=[C:49]4[C:51]3[CH:56]=[CH:55][CH:54]=[C:53]([O:57][CH3:58])[CH:52]=3)[O:40][CH2:39][CH2:38][O:37]2)=[CH:32][CH:31]=1

Komponenten

7

Edukt 5

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 2724682Lithium diisopropylamideHCID 68665640(5-(2-(4-Chlorophenyl)-1,3-dioxolan-2-yl)-2-(methylamino)pyridin-3-yl)(3-methoxyphenyl)methanoneHCID 178418339Butyllithium

Produkt 1

HCID 593347506-(2-(4-chlorophenyl)-1,3-dioxolan-2-yl)-4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-oneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of diisopropylamine (1.32 mL, 9.43 mmol) in THF, a solution of BuLi (7.86 mL, 7.08 mmol, 0.9 M solution in hexane) was added at −20° C. and the resulting mixture was stirred for 30 min. To this solution of LDA, tBuOAc (0.95 mL, 7.08 mmol) was added at −78° C. The mixture was stirred for 30 min and a solution compound G (500 mg, 1.18 mmol) was added to it. The reaction mixture was allowed to warm to RT and stirred overnight. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc (50 mL). The organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by column chromatography to obtain 0.3 g (57%) of compound H off-white solid.

Aufarbeitung

  1. stirringThe mixture was stirred for 30 min
  2. stirringstirred overnight
  3. customThe reaction mixture was quenched with saturated ammonium chloride solution
  4. extractionextracted with EtOAc (50 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1e3c6c1c59224b7bbcf0bde9931ec651
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343996B2

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