Cesium carbonate → 2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine

HRID 1920032

Reaktionsgleichung

Reaktionsgleichung von HRID 1920032
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]3[O:22][CH2:21][CH2:20][O:19]3)=[CH:14][CH:13]=1)=[N:7]2.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][N:40](C(OC(C)(C)C)=O)[CH:41]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:15]1[CH:14]=[CH:13][C:12]([C:6]2[C:5]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[N:11][C:2]=3[C:37]3[CH:38]=[N:39][NH:40][CH:41]=3)[N:7]=2)=[CH:17][CH:16]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 575007255-Chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine

Produkt 1

HCID 575007242-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 5-chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine (1-1, Reference: WO2006135627A2, Dec. 21, 2006) (1.7 g, 4.2 mmol) in DMF (100 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (2.5 g, 8.6 mmol), cesium carbonate (4.2 g, 13 mmol) and Pd(Ph3P)2Cl2 (0.030 g, 0.042 mmol). The reaction mixture was heated at 100° C. under an atmosphere of N2 for 1 hour. The reaction was cooled to room temperature, poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. Purification by silica gel chromatography (EtOAc in hexane) gave 2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine (1-2) as a white solid. MS (M+H)+: calculated 421.47; found 421.51

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by silica gel chromatography (EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8ce21cb9f7d948ce949108a88dd9e60a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168652B2

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