Methanol → 6-Bromoimidazo[1,2-a]pyridin-2-amine

HRID 1162462

Reaktionsgleichung

Reaktionsgleichung von HRID 1162462
[CH2:1]1[N:9]2[C:5](=[N:6][C:7]([NH:10]C(C(F)(F)F)=O)=[CH:8]2)O[CH:3]=[C:2]1[Br:17].[CH2:18]1COCC1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[Br:17][C:2]1[CH:3]=[CH:18][C:5]2[N:9]([CH:8]=[C:7]([NH2:10])[N:6]=2)[CH:1]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 91755269N-(6-bromo-5H-imidazo[2,1-b][1,3]oxazin-2-yl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 441192966-Bromoimidazo[1,2-a]pyridin-2-amineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a 250 mL round-bottomed flask was added N-(6-bromoH-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide (3.50 g, 11 mmol), THF (15 mL), methanol (15 mL), water (15 mL) and potassium carbonate (16 g, 114 mmol). The mixture was stirred at 60° C. for 16 h. After cooling to rt, the mixture was poured into water (100 mL) and extracted with CH2Cl2 (4×75 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0.5 to 5.0% MeOH/CH2Cl2) afforded the title compound (1.01 g, 42%). MS (ESI, positive ion) m/z: 212 (M(79Br)+1).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. extractionextracted with CH2Cl2 (4×75 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated onto silica
  6. customPurification by silica gel chromatography (0.5 to 5.0% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-2348a1d85cd94beba1202cd661fc1e9a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820665B2

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