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Iodo benzene diacetate → 8-(Tert-butyldimethylsilyloxy)-2-(6-fluoro[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

HRID 876439
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 876439
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH:19]=O)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][NH2:29])=[N:26][CH:27]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>O.C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:26]3[CH:27]=[C:22]([F:21])[CH:23]=[CH:24][C:25]3=[N:28][N:29]=1)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 12217721Iodo benzene diacetate2×HCID 199167865-Fluoro-2-hydrazinylpyridineHCID 585670828-(Tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde

Produkt 1

HCID 672311328-(Tert-butyldimethylsilyloxy)-2-(6-fluoro[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

8-(tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde (1.39 g, 4.83 mmol) and 5-fluoro-2-hydrazinylpyridine (1.28 g, 6.04 mmol) were combined in DCM (12.1 mL, 4.83 mmol) at ambient temperature and stirred for 15 minutes. The mixture was cooled to 0° C. followed by addition of iodobenzene diacetate (IBD; 1.87 g, 5.80 mmol). The reaction was warmed to ambient temperature and stirred overnight. Additional IBD (0.8 equivalents, 4.64 mmol) was added and the reaction was allowed to stir at ambient temperature for 48 hours total. The mixture was transferred to a separatory funnel, diluting with water and DCM. The organic phase was washed with saturated aqueous Na2SO3, followed by back extraction of the aqueous phase 2 times with DCM. The organics were combined and washed with brine, dried over Na2SO4, filtered and concentrated to a residue under reduced pressure, followed by purification by flash column chromatography to give the product (1.08 g, 57% yield). MS APCI (+) m/z 395.3 (M+1) detected.

Aufarbeitung

  1. temperatureThe reaction was warmed to ambient temperature
  2. stirringstirred overnight
  3. stirringto stir at ambient temperature for 48 hours total
  4. customThe mixture was transferred to a separatory funnel
  5. washThe organic phase was washed with saturated aqueous Na2SO3
  6. extractionfollowed by back extraction of the aqueous phase 2 times with DCM
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to a residue under reduced pressure
  11. customfollowed by purification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2b7e935582a74667b14622e10f3e2dc7
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987251B2

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