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Sodium Carbonate → 7-Ethyl-4-(4'-(ethylsulfonyl)-2'-fluoro-6-methoxy-[1,1'-biphenyl]-3-yl)-7H-imidazo[4,5-c]pyridazine

HRID 1845991
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1845991
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:13]=2)=[C:8]([F:29])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].Cl[C:31]1[C:32]2[N:39]=[CH:38][N:37]([CH2:40][CH3:41])[C:33]=2[N:34]=[N:35][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:40]([N:37]1[C:33]2[N:34]=[N:35][CH:36]=[C:31]([C:14]3[CH:13]=[C:12]([C:9]4[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:7][C:8]=4[F:29])[C:17]([O:18][CH3:19])=[CH:16][CH:15]=3)[C:32]=2[N:39]=[CH:38]1)[CH3:41]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 552967654-chloro-7-ethyl-7H-imidazo(4,5-c)pyridazineHCID 867232202-(4'-(Ethylsulfonyl)-2'-fluoro-6-methoxy-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 867232197-Ethyl-4-(4'-(ethylsulfonyl)-2'-fluoro-6-methoxy-[1,1'-biphenyl]-3-yl)-7H-imidazo[4,5-c]pyridazineAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To 2-(4′-(ethylsulfonyl)-2′-fluoro-6-methoxy-[1,1′-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 69, 90 mg, 0.21 mmol) in dioxane (2.5 mL) and water (1 mL) was added 4-chloro-7-ethyl-7H-imidazo[4,5-c]pyridazine (Preparation 8, 40 mg, 0.21 mmol) and sodium carbonate (68 mg, 0.64 mmol). The reaction was degassed and tetrakis(triphenylphosphine) palladium(0) (25 mg, 0.02 mmol) was added. The reaction was further degassed and then heated to 110° C. for 2 hours and then cooled to room temperature. The reaction mixture was diluted with EtOAc (40 mL) was passed through celite and the solvent removed in vacuo. The crude material was purified by reverse phase column chromatography eluting with a gradient of 0.1% formic acid in MeCN/water. The resulting residue was dissolved in DMSO (1 mL) and purified using preparative HPLC to give the title compound as a colourless solid in 26% yield, 24 mg.

Aufarbeitung

  1. customThe reaction was degassed
  2. customThe reaction was further degassed
  3. temperaturecooled to room temperature
  4. additionThe reaction mixture was diluted with EtOAc (40 mL)
  5. customthe solvent removed in vacuo
  6. customThe crude material was purified by reverse phase column chromatography
  7. washeluting with a gradient of 0.1% formic acid in MeCN/water
  8. dissolutionThe resulting residue was dissolved in DMSO (1 mL)
  9. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-daa71901b4f54da2bee0c04c4dd804cc
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952008B2

Notizen zur Reaktion

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