Pyridine → 2-(4-Chlorophenyl)-5-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)furo[3,2-c]pyridin-4(5H)-one

HRID 60377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60377
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][NH:12][C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH:18]1([C:21]2[N:22]=[C:23]3[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][N:24]3[C:32]=2[CH3:33])[CH2:20][CH2:19]1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:26]4[CH:27]=[CH:28][C:23]5[N:24]([C:32]([CH3:33])=[C:21]([CH:18]6[CH2:20][CH2:19]6)[N:22]=5)[CH:25]=4)[C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 580155582-(4-chlorophenyl)-5H-furo[3,2-c]pyridine-4-oneHCID 89690439HCID 89690439, Verbindung

Produkt 1

HCID 718165182-(4-Chlorophenyl)-5-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)furo[3,2-c]pyridin-4(5H)-oneAusbeute 5,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 2-(4-chlorophenyl)furo[3,2-c]pyridin-4(5H)-one (100 mg), (2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)boronic acid (106 mg), copper(II) acetate (4.99 mg), pyridine (0.066 mL), MS-4A (48.9 mg) and DMF (5.0 mL) was stirred at room temperature for 4 hr and at 50° C. overnight. After filtration of the obtained mixture through Celite, the filtrate was poured into 1 N hydrochloric acid and extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained solid was washed with ethanol to give the title compound (10.0 mg) as a pale brown solid.

Aufarbeitung

  1. filtrationAfter filtration of the obtained mixture through Celite
  2. additionthe filtrate was poured into 1 N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe obtained solid was washed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2034a445db9f4e60aba5da68a027397c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440987B2

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