Cesium carbonate → 4'-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-3'-fluoro-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

HRID 571061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571061
[F:1][C:2]1[C:3]([N:9]2[CH:14]=[CH:13][C:12](=[O:15])[C:11]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[CH:10]2)=[N:4][CH:5]=[CH:6][C:7]=1I.[Cl:26][C:27]1[C:28](B2OC(C)(C)C(C)(C)O2)=[C:29]2[CH:35]=[CH:34][N:33]([Si](C(C)C)(C(C)C)C(C)C)[C:30]2=[N:31][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[Cl:26][C:27]1[C:28]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([N:9]3[CH:14]=[CH:13][C:12](=[O:15])[C:11]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[CH:10]3)[C:2]=2[F:1])=[C:29]2[CH:35]=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 453617775-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 674184733'-fluoro-4'-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

Produkt 1

HCID 866802754'-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-3'-fluoro-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a room temperature solution of 132 mg (0.292 mmol) 3′-fluoro-4′-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2′-bipyridin-4-one in 2 mL THF in a 5 mL microwave vial (Biotage) were added 253 mg (0.584 mmol) 5-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine, 1 mL 1.0 M cesium carbonate (1.0 mmol), and 23.8 mg (0.029 mmol) 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex. The vial was sealed and the reaction mixture was heated at 135° C. under microwave irradiation for 15 minutes, then cooled. The organic layer was separated, washed with 1 mL water, dried over Na2SO4, filtered, stirred over Quadrapure TU resin (Aldrich), concentrated in vacuo, and used without further purification.

Aufarbeitung

  1. customThe vial was sealed
  2. temperaturecooled
  3. customThe organic layer was separated
  4. washwashed with 1 mL water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d01eb79885d549308c062da0ba9abb8f
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024032B2

Notizen zur Reaktion

Wird geladen…