Potassium Carbonate → 4-{4-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 69220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69220
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]=[CH:17][CH:16]=[CH:15]4)=[CH:9][N:10]=2)[N:7]=1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH:40]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:38]=[N:37]2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+]>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.COCCOC>[C:23]([O:27][C:28]([N:30]1[CH2:31][CH2:32][CH:33]([N:36]2[CH:40]=[C:39]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([CH2:11][C:12]5[CH:13]=[C:14]6[C:19](=[CH:20][C:21]=5[F:22])[N:18]=[CH:17][CH:16]=[CH:15]6)=[CH:9][N:10]=4)[N:7]=3)[CH:38]=[N:37]2)[CH2:34][CH2:35]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 45480279tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylateHCID 581475166-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline

Produkt 1

HCID 686342444-{4-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A microwave tube was charged with 6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Stage 180.2, 500 mg, 1.599 mmol), 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (prepared as described in published patent application WO 2007/066185 p. 9 & 10; 905 mg, 2.398 mmol), Pd(PPh3)2Cl2 (56 mg), 2 M K2CO3 (2.158 mL) and DME (5 mL) and was heated at 90° C. for 2 h under stirring. The RM was extracted with EtOAc and aqueous NaHCO3. The organic layer was dried and concentrated in vacuo. The reside was dried under vacuum (12 mbar) for 3 days to afford the title compound (tR 4.5 min (conditions 3), MH+=528)

Aufarbeitung

  1. extractionThe RM was extracted with EtOAc and aqueous NaHCO3
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customThe reside was dried under vacuum (12 mbar) for 3 days

Quellen und Nachweise

ORD-Eintrag
ord-78efa87f036b4d45ba91e0768e3e2b14
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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