Potassium Fluoride → HCID 18436712, Verbindung

HRID 456717

Reaktionsgleichung

Reaktionsgleichung von HRID 456717
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15](I)=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][S:27][C:28]1[N:33]=[C:32]([Sn](CCCC)(CCCC)CCCC)[CH:31]=[CH:30][N:29]=1.[F-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([C:30]3[CH:31]=[CH:32][N:33]=[C:28]([S:27][CH3:26])[N:29]=3)=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 522689Potassium FluorideHCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 184367138-(Benzyloxy)-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine

Produkt 1

HCID 18436712HCID 18436712, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 8-(benzyloxy)-2-(4-fluorophenyl)-3-iodoimidazo[1,2-a]pyridine (0.15 g, 0.35 mmol) and dichlorobis(triphenylphosphine)palladium(II) (30 mg, 0.0035 mmol) in toluene (3 mL) was added 2-(methylsulfanyl)-4-(tributylstannyl)pyrimidine (0.19 g, 0.46 mmol). The mixture was heated to 110° C. in a sealed tube for 16 hours. The reaction was allowed to cool and was diluted with ethyl acetate before being poured into a 10% aqueous potassium fluoride solution. The mixture was extracted with ethyl acetate. The organic phase was concentrated and the residue purified by silica chromatography, eluting with dichloromethane and then 5% acetone in dichloromethane to yield 60 mg (39%) of 8-(benzyloxy)-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)pyrimidin-4-yl]imidazo[1,2-a]pyridine. 1H NMR (CDCl3): δ 9.18 (d, 1H), 8.33 (d, 1H), 7.68 (dd, 2H), 7.54 (2H), 7.41 (m, 3H), 7.16 (t, 2H), 6.83 (m, 2H), 6.70 (d, 1H), 5.46 (s, 2H), 2.67 (s, 3H). MS m/z 443 (M+1).

Aufarbeitung

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate
  3. concentrationThe organic phase was concentrated
  4. customthe residue purified by silica chromatography
  5. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-cedf43f6a5de43d19e6c6ac89c38e91c
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186714B2

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