Potassium Carbonate → [2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanone

HRID 875439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875439
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([C:11]2[C:19]3[C:14](=[CH:15][N:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])=[C:4]([Cl:20])[CH:3]=1.C(OC([N:28]1[C:32]([CH3:33])=[C:31](B(O)O)[C:30]([CH3:37])=[N:29]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[Cl:8][C:6]1[CH:7]=[C:2]([C:31]2[C:32]([CH3:33])=[N:28][NH:29][C:30]=2[CH3:37])[CH:3]=[C:4]([Cl:20])[C:5]=1[C:9]([C:11]1[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:10]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 467398121-BOC-3,5-dimethylpyrazole-4-boronic acidHCID 71061835(4-Bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone

Produkt 1

HCID 86720645[2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanoneAusbeute 23,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24290Palladium ChlorideKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of (4-bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (50 mg, 0.135 mmol), [1-(tert-butoxycarbonyl)-3,5-dimethyl-1H-pyrazol-4-yl]boronic acid (52 mg, 0.162 mmol), potassium carbonate (55 mg, 0.4 mmol), water (0.5 mL) and 1,1′bis(diphenylphosphino)ferrocene]dichloropalladium (II) (11 mg, 0.0135 mmol) in 1,4 dioxane (2 mL) was heated at 100° C. for 2 hours in a sealed vial. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting crude mass was purified by preparative thin layer chromatography using methanol in dichloromethane (10%) to afford [2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (0.012 g, 23%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe resulting crude mass was purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3e257a33c46b4a7089fedaa33d414efe
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980911B2

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