Water → N-{5-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}benzenecarboxamide

HRID 876234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876234
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1.[F:17][C:18]([F:30])([F:29])[O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.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.CN(C=O)C>[F:17][C:18]([F:29])([F:30])[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[C:4]([NH:8][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])[CH:5]=[N:6][CH:7]=2)=[CH:22][CH:21]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 66701388N-(5-bromopyridin-3-yl)benzamide

Produkt 1

HCID 66701354N-{5-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}benzenecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

At 50° C., 11.8 g (41.4 mmol) of N-(5-bromopyridin-3-yl)benzamide, 12.8 g (62.1 mmol) of [4-(trifluoromethoxy)phenyl]boronic acid and 11.4 g (82.7 mmol) of potassium carbonate were dissolved in 70 ml of 1,2-dimethoxyethane, 21 ml of water and 156 ml of DMF. The mixture was flushed with argon, 0.24 g (0.2 mmol) of tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred at 85° C. for 12 h. The reaction mixture was concentrated slightly on a rotary evaporator, diluted with water and extracted with dichloromethane. The organic phase was concentrated under reduced pressure and the residue was triturated with methyl tert-butyl ether. The solid was filtered off and the filtrate was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 2:1=>1:5). The separated solid and the appropriate fraction from the chromatography were combined. Yield: 6.7 g (45% of theory)

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated slightly on a rotary evaporator
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. concentrationThe organic phase was concentrated under reduced pressure
  6. customthe residue was triturated with methyl tert-butyl ether
  7. filtrationThe solid was filtered off
  8. customthe filtrate was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 2:1=>1:5)

Quellen und Nachweise

ORD-Eintrag
ord-e24b83e5b78147a59c760b1f47d4a4c6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987248B2

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