Cesium fluoride → 4-(1,3-dihydroisoindol-2-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline

HRID 1469090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469090
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[CH:21]=[C:22]4[CH:28]=[CH:27][N:26]([Si](C(C)C)(C(C)C)C(C)C)[C:23]4=[N:24][CH:25]=3)[CH:18]=2)[N:13]=[CH:12][N:11]=1.[F-].[Cs+]>C(#N)C>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][N:2]1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[CH:21]=[C:22]4[CH:28]=[CH:27][NH:26][C:23]4=[N:24][CH:25]=3)[CH:18]=2)[N:13]=[CH:12][N:11]=1

Komponenten

4

Edukt 2

HCID 25953Cesium fluorideHCID 675137734-(1,3-dihydroisoindol-2-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline

Produkt 1

HCID 569666644-(1,3-dihydroisoindol-2-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolineAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

0.12 g of 4-(1,3-dihydroisoindol-2-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]-pyridin-5-yl)quinazoline and 0.05 g of caesium fluoride in 1 ml of acetonitrile are stirred at 25° C. in a flask until the reaction is complete (HPLC check about 24 hours). A precipitate precipitates out of the reaction solution. This is filtered off, rinsed with water and dried, giving 0.08 g of 4-(1,3-dihydroisoindol-2-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline (“A2”) as white solid (yield 95%, content 96%); MS-FAB (M+H+)=363.8; Rf (polar method): 1.63 min;

Aufarbeitung

  1. custom(HPLC check about 24 hours)
  2. customA precipitate precipitates out of the reaction solution
  3. filtrationThis is filtered off
  4. washrinsed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-492fed9de40940538ad86a2b55b5da4e
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006255B2

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