Water → 2-(3-Methoxy-4-pyridin-3-ylphenyl)-1,3-benzoxazole

HRID 7761

Reaktionsgleichung

Reaktionsgleichung von HRID 7761
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:8]=1[O:22][CH3:23])(=O)=O.O.C([O-])([O-])=O.[K+].[K+].[N:33]1[CH:38]=[CH:37][CH:36]=[C:35](B(O)O)[CH:34]=1>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][O:22][C:8]1[CH:9]=[C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:11]=[CH:12][C:7]=1[C:35]1[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 219909894-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl trifluoromethanesulfonate

Produkt 1

HCID 101717852-(3-Methoxy-4-pyridin-3-ylphenyl)-1,3-benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

The solution of 4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl trifluoromethanesulfonate (148 mg, 0.4 mmol) in 6 mL of 2:1 DMF:H2O was degassed via Argon for 10 min. Then K2CO3 (137 mg, 0.99 mmol), Pd(Ph3P)4 (23 mg, 0.02 mmol), n-Bu4NBr (128 mg, 0.40 mmol) and 3-Pyridylboronic acid (73 mg, 0.60 mmol) were added at 22° C. The resulting mixture was then heated at 75° C. for 1 h under Argon. Cooled the reaction mixture to 22° C., then filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to give after purification by flash chromatography (silica gel, 3:1; hexanes:EtOAc) the desired compound as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.83 (d, 1H), 8.60 (dd, 1H), 7.92 (m, 3H), 7.81 (m, 1H), 7.62 (m, 1H), 7.48 (d, 1H), 7.39 (m, 3H), 3.98 (s, 3H). MS (ESI) 303 (M+H)+.

Aufarbeitung

  1. temperatureCooled the reaction mixture to 22° C.
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give
  5. customafter purification by flash chromatography (silica gel, 3:1; hexanes:EtOAc) the desired compound as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-1e752cd1bb8744e3a7f516e7c7fa0f3a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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