Pyridine → HCID 59272956, Verbindung

HRID 2423082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423082
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[C:10]=1[N:9]([C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:14]([F:13])[CH:15]=1)[N:8]=[CH:7]2

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 592729777-Fluoro-4-methoxy-1H-indazole

Produkt 1

HCID 59272956HCID 59272956, VerbindungAusbeute 25,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

7-Fluoro-4-(methyloxy)-1H-indazole (D26) (500 mg, 3.01 mmol), the {3-fluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid (1.48 g, 6.02 mmol), copper (II) acetate (820 mg, 4.51 mmol), powdered molecular sieves (550 mg) and pyridine (0.49 mL, 6.02 mmol) in DCM (15 mL) were stirred at room temperature in the presence of air. After 4 hours the mixture was filtered through a pad of celite and washed with water. The aqueous was re-extracted with DCM (3×) and the combined organics were washed with brine and dried over MgSO4. The crude (1.71 g) was purified by flash chromatography (Biotage SP4) with a gradient of EtOAc (0 to 20%) in hexane to afford 286 mg of title compound (D27).

Aufarbeitung

  1. filtrationAfter 4 hours the mixture was filtered through a pad of celite
  2. washwashed with water
  3. extractionThe aqueous was re-extracted with DCM (3×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude (1.71 g) was purified by flash chromatography (Biotage SP4) with a gradient of EtOAc (0 to 20%) in hexane

Quellen und Nachweise

ORD-Eintrag
ord-b28f2ed5f90d4da5a30e70e9a81bfdb0
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960563B2

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