Sodium Carbonate → 8-Methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 269029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269029
Br[C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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>[CH3:11][C:4]1[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)[CH:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 52606476-Bromo-8-methylimidazo(1,2-a)pyridine

Produkt 1

HCID 670011108-Methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A mixture of 6-bromo-8-methyl-imidazo[1,2-a]pyridine (example C.20 step 1) (7.0 g, 33 mmol), commercially available 4-(trifluoromethyl)phenylboronic acid (6.929 g, 36 mmol), Pd(PPh3)4 (383 mg, 1 mol %) and 1M Na2CO3-solution (77 mL, 77 mmol) in DME (150 mL) was stirred at reflux for 1 h. Cooled to 23° C., diluted with water, extracted with EtOAc, washed the organic layer with brine, dried over MgSO4. Removal of the solvent in vacuum left a brown solid, which was purified by silica gel column chromatography with EtOAc/MeOH to give the title compound as a white solid (8.29 g, 91%). MS (ISP) 277.1 [(M+H)+].

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. extractionextracted with EtOAc
  3. washwashed the organic layer with brine
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent in vacuum
  6. waitleft a brown solid, which
  7. customwas purified by silica gel column chromatography with EtOAc/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-ea85f3bb56034e53bd8415f1ae96cc30
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446113B2

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