Sodium Carbonate → N-[3-(1-i-butyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

HRID 45894

Reaktionsgleichung

Reaktionsgleichung von HRID 45894
Br[C:2]1[C:3]([C:11]2[C:12]([F:30])=[C:13]([NH:18][S:19]([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])(=[O:21])=[O:20])[CH:14]=[CH:15][C:16]=2[F:17])=[N:4][N:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH:6]=1.CC1(C)C(C)(C)OB([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:7]([N:5]1[CH:6]=[C:2]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[C:3]([C:11]2[C:12]([F:30])=[C:13]([NH:18][S:19]([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])(=[O:21])=[O:20])[CH:14]=[CH:15][C:16]=2[F:17])=[N:4]1)[CH:8]([CH3:9])[CH3:10]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine2×HCID 67184852N-{3-[4-bromo-1-(2-methylpropyl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}-2,5-difluorobenzenesulfonamide

Produkt 1

HCID 44622143N-[3-(1-i-butyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator2×HCID 80711,2-DimethoxyethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of tetrakis(triphenylphosphine)palladium(0) (0.035 g, 0.03 mmol) in dimethoxyethane (1 mL), N-{3-[4-bromo-1-(2-methylpropyl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}-2,5-difluorobenzenesulfonamide (0.09 g, 0.18 mmol) in dimethoxyethane (1 mL) was added and the mixture was insufflated with nitrogen for 5 min. A solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.08 g, 0.4 mmol)) in dimethoxyethane (1 mL) was added and the mixture was insufflated with nitrogen for 10 min, then 2 M sodium carbonate solution (1 mL) was added and the mixture was heated at 110° C. in a microwave cavity for 1 h. More tetrakis(triphenylphosphine)palladium(0) (0.012 g, 0.01 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.016 g, 0.08 mmol) were added and the process was resumed for 0.5 h. The mixture was cooled and the organic phase was concentrated. The crude oil was purified by flash chromatography (eluant: dichloromethane/methanol 30:1). The title compound was obtained as a white solid (0.025 g, 28%).

Aufarbeitung

  1. waitthe mixture was insufflated with nitrogen for 10 min
  2. waitthe process was resumed for 0.5 h
  3. temperatureThe mixture was cooled
  4. concentrationthe organic phase was concentrated
  5. customThe crude oil was purified by flash chromatography (eluant: dichloromethane/methanol 30:1)

Quellen und Nachweise

ORD-Eintrag
ord-1ac0cc4657f7487ba7f57ba70b46469d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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