Tetrahydrofuran → 4-(3-(4-(Pyridin-3-yloxy)phenyl)-1,2,4-oxadiazol-5-yl)phenol

HRID 2167340

Reaktionsgleichung

Reaktionsgleichung von HRID 2167340
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:32]=[CH:31][C:23]([O:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1>CO.[Pd]>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:24][C:23]2[CH:22]=[CH:21][C:20]([C:17]3[N:16]=[C:15]([C:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=4)[O:19][N:18]=3)=[CH:32][CH:31]=2)[CH:26]=1

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 595339523-(4-(5-(4-(Benzyloxy)phenyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyridine

Produkt 1

HCID 1358782084-(3-(4-(Pyridin-3-yloxy)phenyl)-1,2,4-oxadiazol-5-yl)phenolAusbeute 1,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

In a single neck round bottom flask fitted with a condenser, 3-(4-(5-(4-(Benzyloxy)phenyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyridine (224 mg, 531 μmol) was suspended in methanol (5.0 mL) and THF (5.0 mL) and then 10% Pd/C (1.0 mg, 36 μmol) was added. The reaction vessel was sealed and the solution was stirred under H2 at 55° C. for 23 hours. The hot solution was filtered through Celite and the pad was washed with methanol (20 mL). The solvent was removed under reduced pressure. The solid residue was purified by silica gel column chromatography (EtOAc/Hex 1:2) to give the product as a white solid (2 mg, 1%). 1H NMR (500 MHz, DMSO-d6) δ(ppm): 7.00 (2H, d, J=9.0 Hz), 7.23 (1H, d, J=9.0 Hz), 7.05 (1H, ddd, J=8.4, 4.8, 0.8 Hz), 7.61 (1H, ddd, J=8.4, 2.8, 1.4 Hz), 8.02 (2H, d, J=9.0 Hz), 8.01 (2H, d, J=9.0 Hz), 8.46 (1H, dd, J=4.7, 1.3 Hz), 8.21 (1H, d, J=2.8 Hz) 10.58 (1H, s). MS (FAB+): 332 (MH+). HRMS for C19H13N3O3 (MH+): calculated: 332.1035; found 332.1013.

Aufarbeitung

  1. customIn a single neck round bottom flask fitted with a condenser
  2. customThe reaction vessel was sealed
  3. filtrationThe hot solution was filtered through Celite
  4. washthe pad was washed with methanol (20 mL)
  5. customThe solvent was removed under reduced pressure
  6. customThe solid residue was purified by silica gel column chromatography (EtOAc/Hex 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-ffcb7b2cb1a6425690910f2eb772db7c
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045442B2

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