Sodium Carbonate → 4-tert-Butyl-N-{3-[6-(4-fluoro-3-nitro-phenylamino)4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamide

HRID 551858

Reaktionsgleichung

Reaktionsgleichung von HRID 551858
Br[C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:21]([C:25]1[CH:49]=[CH:48][C:28]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34](B3OC(C)(C)C(C)(C)O3)[C:33]=2[CH3:47])=[O:30])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC>[C:21]([C:25]1[CH:49]=[CH:48][C:28]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:2]3[N:3]=[C:4]([NH:10][C:11]4[CH:16]=[CH:15][C:14]([F:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=4)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=3)[C:33]=2[CH3:47])=[O:30])=[CH:27][CH:26]=1)([CH3:24])([CH3:22])[CH3:23]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 587289745-Bromo-3-[(4-fluoro-3-nitrophenyl)amino]-1-methylpyrazin-2(1H)-oneHCID 587289934-(tert-Butyl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide

Produkt 1

HCID 587291254-tert-Butyl-N-{3-[6-(4-fluoro-3-nitro-phenylamino)4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamideAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-3-(4-fluoro-3-nitro-phenylamino)-1-methyl-1H-pyrazin-2-one (1) (8.8 g; 25.7 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (11.1 g; 28.3 mmol), tetrakis(triphenylphosphine)palladium (1.48 g; 1.28 mmol), 1N sodium carbonate (77 mL; 77 mmol), and 1,2-dimethoxyethane (100 mL) was heated at 100 degrees in a sealed pressure vessel for 16 hr. The mixture was cooled to room temperature, filtered, and the residue washed with water (3×60 mL). The solid was slurried with ethyl acetate for 1 hr, filtered, and washed with diethyl ether to give 4-tert-butyl-N-{3-[6-(4-fluoro-3-nitro-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamide (2) as a dull yellow solid (13 g).

Aufarbeitung

  1. temperaturewas heated at 100 degrees in a sealed pressure vessel for 16 hr
  2. filtrationfiltered
  3. washthe residue washed with water (3×60 mL)
  4. filtrationfiltered
  5. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a4dcf716925f42399d388c9da9e81b05
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947835B2

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