Chloroacetone → 6-Bromo-2,7-dimethyl-8-(3-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 1497756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497756
[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH2:21][C:22](=O)[CH3:23]>>[NH3:6].[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)[C:5]2[N:6]([CH:21]=[C:22]([CH3:23])[N:8]=2)[CH:7]=1

Komponenten

4

Edukt 2

HCID 6571Chloroacetone2×HCID 867080865-Bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine

Produkt 2

HCID 222AmmoniaHCID 867080946-Bromo-2,7-dimethyl-8-(3-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridineAusbeute 163,2 %

Versuchsvorschrift

5-Bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine (Int. 1, 500 mg, 1.51 mmol) and 1-chloropropan-2-one (144 μL, 1.81 mmol) were heated at reflux in IMS (3 mL) for 18 hrs then a further quantity of 1-chloropropan-2-one (144 μL) was added. Heating was continued for 24 hrs then the solvent was evaporated in vacuo and the residue was purified by flash chromatography eluting with a gradient of 0-50% EtOAc in cyclohexane then 0-10% (2N NH3 in MeOH) in DCM to give the title compound as a cream solid (455 mg).

Aufarbeitung

  1. temperatureHeating
  2. customthe solvent was evaporated in vacuo
  3. customthe residue was purified by flash chromatography
  4. washeluting with a gradient of 0-50% EtOAc in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-5c83fcb9a25f40c491db991ab41b76bd
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199984B2

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