Potassium Phosphate, Tribasic → 2-(2,6-Difluorophenyl)-5-(4-morpholinophenylamino)oxazole-4-carbonitrile

HRID 389749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389749
Br[C:2]1[O:6][C:5]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])=[N:4][C:3]=1[C:15]#[N:16].[O:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:7]=1[C:5]1[O:6][C:2]([NH:27][C:26]2[CH:25]=[CH:24][C:23]([N:20]3[CH2:21][CH2:22][O:17][CH2:18][CH2:19]3)=[CH:29][CH:28]=2)=[C:3]([C:15]#[N:16])[N:4]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 595875125-Bromo-2-(2,6-difluorophenyl)oxazole-4-carbonitrile

Produkt 1

HCID 595874532-(2,6-Difluorophenyl)-5-(4-morpholinophenylamino)oxazole-4-carbonitrileAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A solution of palladium acetate (0.0057 g, 0.025 mmol) and (±)-2,2″-bis(diphenylphosphino)-1,1″-binaphthalene (0.015 g, 0.024 mmol) in DMF (7.1 mL) was stirred at room temperature for 3 minutes. Then 5-bromo-2-(2,6-difluorophenyl)oxazole-4-carbonitrile (0.100 g, 0.35 mmol), 4-morpholinoaniline (0.250 g, 1.40 mmol) and potassium phosphate tribasic (0.149 g, 0.70 mmol) were added and the mixture heated in the microwave for 3 minutes at 180° C. The reaction was diluted with EtOAc and washed with water. The organic phase was passed through a MP-SH resin cartridge, dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using a gradient 10-100% EtOAc in hexanes to afford 2-(2,6-difluorophenyl)-5-(4-morpholinophenylamino)oxazole-4-carbonitrile (0.035 g, 0.09 mmol, 26%) as an off white solid. 1H NMR (DMSO) δ 3.08 (4H, t), 3.74 (4H, t), 6.97 (2H, d), 7.24 (2H, d), 7.33 (2H, t), 7.64 (1H, m), 10.58 (1H, s). LCMS (2) Rt: 2.92 min; m/z (ES+) 383.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-df08ba70b41041518a503c3f763758cc
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378095B2

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