Ammonium Chloride → 2-Trifluoroacetamido-3-phenyl-6-(2,3-difluorobenzoyl)-imidazo[1,2-a]pyridine

HRID 277933

Reaktionsgleichung

Reaktionsgleichung von HRID 277933
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1Br.C([Li])CCC.[F:15][C:16]([F:42])([F:41])[C:17]([NH:19][C:20]1[N:21]=[C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:33])N(C)OC)=[CH:24][N:23]2[C:34]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:18].[NH4+].[Cl-]>C1COCC1>[F:42][C:16]([F:15])([F:41])[C:17]([NH:19][C:20]1[N:21]=[C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:33])[C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])=[CH:24][N:23]2[C:34]=1[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:18]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 27332601-Bromo-2,3-difluorobenzeneHCID 22626677HCID 22626677, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 226267592-Trifluoroacetamido-3-phenyl-6-(2,3-difluorobenzoyl)-imidazo[1,2-a]pyridineAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2,3-difluorobromobenzene (471 ml, 4.206 mmol) in dry THF (20 mL) was added a solution of n-butyl lithium (1.6M in hexanes, 2.63 mL) at −78° C. The resulting yellow solution was stirred at the same temperature for 70 minutes, then a solution of 2-trifluoroacetamido-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine (0.500 g, 1.28 mmol) in dry THF (20 mL), was added dropwise via a cannula. The red-orange solution was allowed to warm over 60 minutes. Saturated NH4Cl was added and the mixture was stirred for 25 minutes before extracting with EtOAc. The organic layer was washed with brine, dried (Na2SO4), concentrated in vacuo and purified by column chromatography (CH2Cl2/CH3CN 4/1) to give 390 mg of an orange solid. (69%). MS(FAB), NMR.

Aufarbeitung

  1. temperatureto warm over 60 minutes
  2. stirringthe mixture was stirred for 25 minutes
  3. extractionbefore extracting with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (CH2Cl2/CH3CN 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-c7a2d11d6ca34c91a36a22795103a530
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358971B1

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