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

HRID 45892

Reaktionsgleichung

Reaktionsgleichung von HRID 45892
Br[C:2]1[C:3]([C:8]2[C:9]([F:27])=[C:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])(=[O:18])=[O:17])[CH:11]=[CH:12][C:13]=2[F:14])=[N:4][N:5]([CH3:7])[CH:6]=1.CC1(C)C(C)(C)OB([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=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>[CH3:7][N:5]1[CH:6]=[C:2]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)[C:3]([C:8]2[C:9]([F:27])=[C:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])(=[O:18])=[O:17])[CH:11]=[CH:12][C:13]=2[F:14])=[N:4]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 67183603N-[3-(4-bromo-1-methyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluorobenzenesulfonamide

Produkt 1

HCID 44622139N-[3-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) in dimethoxyethane (3 mL), N-[3-(4-bromo-1-methyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluorobenzenesulfonamide (0.14 g, 0.3 mmol) in dimethoxyethane (3 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 (0.13 g, 0.63 mmol) in dimethoxyethane (3 mL) was added and the mixture was insufflated with nitrogen for 10 min, then 2 M sodium carbonate solution (2.5 mL) was added and the mixture was heated at 110° C. in a microwave cavity for 3 h. The mixture was cooled and the organic phase was concentrated. The crude oil was purified by flash chromatography (eluant: dichloromethane/ethyl acetate 1:1). The title compound was obtained as a white solid (0.05 g, 36%).

Aufarbeitung

  1. waitthe mixture was insufflated with nitrogen for 10 min
  2. temperatureThe mixture was cooled
  3. concentrationthe organic phase was concentrated
  4. customThe crude oil was purified by flash chromatography (eluant: dichloromethane/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5560b44fa49d467ab22cf4b43096828a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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