4-Fluorophenol → 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((4-fluorophenoxy)methyl)pyridin-2(1H)-one

HRID 2202991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202991
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][C:13]4=[O:20])=[CH:8][N:7]3[C:21]=2[CH3:22])[CH2:3][CH2:2]1.[F:23][C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([CH2:18][O:19][C:27]5[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=5)=[CH:14][C:13]4=[O:20])=[CH:8][N:7]3[C:21]=2[CH3:22])[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 97324-FluorophenolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 89690337HCID 89690337, Verbindung

Produkt 1

HCID 896901851-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((4-fluorophenoxy)methyl)pyridin-2(1H)-oneAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-(hydroxymethyl)pyridin-2(1H)-one (150 mg), 4-fluorophenol (85 mg) and tributylphosphine (307 mg) in THF (20 ml) was added 1,1′-(azodicarbonyl)dipiperidine (386 mg), and the mixture was stirred at 60° C. for 5 h. The reaction mixture was cooled to room temperature, concentrated in vacuo, and diluted with DCM. The mixture was washed with water and brine successively, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (MeOH/DCM) followed by preparative HPLC to afford the title compound (24 mg) as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with DCM
  4. washThe mixture was washed with water and brine successively
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-5c701066adfc4d5c99c1c178d08b2582
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365540B2

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