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Potassium Carbonate → 2-dimethylamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246436
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2246436
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[C:11]([N:13]([CH3:15])[CH3:14])[NH:12][C:4]=2[CH:3]=1.[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[C:28]([F:31])([F:30])[F:29])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:14][N:13]([CH3:15])[C:11]1[NH:12][C:4]2[CH:3]=[C:2]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH2:16][CH3:17])=[C:20]([C:28]([F:29])([F:31])[F:30])[CH:21]=3)[N:7]=[C:6]([C:8]#[N:9])[C:5]=2[N:10]=1
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 445581844-Ethoxy-3-(trifluoromethyl)benzeneboronic acidHCID 589381326-chloro-2-dimethylamino-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Produkt 1

HCID 589381232-dimethylamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrileAusbeute 3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A suspension of 6-chloro-2-dimethylamino-1H-imidazo[4,5-c]pyridine-4-carbonitrile (100 mg, 0.45 mmol), 4-ethoxy-3-trifluoromethyl-phenyl boronic acid (198 mg, 0.88 mmol) tetrakis(triphenylphosphine)palladium(0) (50 mg, ˜10 mol %) and potassium carbonate (193.0 mg, 1.39 mmol) in THF (3 ml) was heated to 130° C. for 6 minutes in the “Smith” microwave. The crude mixture was concentrated under reduced pressure to remove THF before partitioning between ethyl acetate and water. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The material was then dissolved in DMSO and purified in aliquots by preparative HPLC. The desired fractions were collected and concentrated to give a white solid which was washed with ether to afford 2-dimethylamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (5.0 mg)

Aufarbeitung

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. customto remove THF
  3. custombefore partitioning between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe material was then dissolved in DMSO
  8. custompurified in aliquots by preparative HPLC
  9. customThe desired fractions were collected
  10. concentrationconcentrated
  11. customto give a white solid which
  12. washwas washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-102f7f63ac584b16ad4ba8611f9f5416
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07687515B2

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