2,5-Dichlorophenol → [3-(2,5-Dichloro-phenoxy)-pyridin-4-yl]-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-methanone

HRID 1877438

Reaktionsgleichung

Reaktionsgleichung von HRID 1877438
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH2:12][CH2:11]1)=[O:9].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[OH:28].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC#N.CC#N.CC#N.CC#N.F[P-](F)(F)(F)(F)F.[Cu+]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[O:28][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH2:12][CH2:11]1)=[O:9]

Komponenten

6

Edukt 3

HCID 662,5-DichlorophenolHCID 10796Cesium carbonateHCID 67378149(3-Bromo-pyridin-4-yl)-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-methanone

Produkt 1

HCID 59294493[3-(2,5-Dichloro-phenoxy)-pyridin-4-yl]-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-methanoneAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11068737tetrakis(acetonitrile)copper(I) hexafluorophosphateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of (3-bromo-pyridin-4-yl)-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-methanone (80 mg, 0.25 mmol, 1.0 equiv) and 2,5-dichloro-phenol (49 mg, 0.30 mmol, 1.2 equiv; [CAS RN 583-78-8]) in anhydrous toluene (1.5 mL) was added caesium carbonate (204 mg, 0.63 mmol, 2.5 equiv; [CAS RN 534-17-8]) and tetrakis(acetonitrile)copper(I) hexafluorophosphate (18.7 mg, 0.050 mmol, 0.2 equiv; [CAS RN 64443-05-6]). The reaction mixture was heated by microwave irradiation to 160° C. for 2 h. Purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 17 mg (17%) of the title compound as a light brown solid. MS (ISP): 400.9 [M+H]+.

Aufarbeitung

  1. customPurification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column
  2. customequipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps
  3. washa Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-3114446e0bee4e048650da85c486e31f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309734B2

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