Cesium carbonate → 3-((3-(3-(4-fluorophenoxy)azetidin-1-yl)phenyl)amino)-N-methylbenzamide

HRID 522932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522932
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([NH:26][CH3:27])=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:4]3[CH:3]=[C:2]([NH:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([NH:26][CH3:27])=[O:25])[CH:7]=[CH:6][CH:5]=3)[CH2:9]2)=[CH:14][CH:15]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 6765263-Amino-N-methylbenzamideHCID 673548151-(3-Bromophenyl)-3-(4-fluorophenoxy)azetidine

Produkt 1

HCID 533728563-((3-(3-(4-fluorophenoxy)azetidin-1-yl)phenyl)amino)-N-methylbenzamideAusbeute 23,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1-(3-bromophenyl)-3-(4-fluorophenoxy)azetidine (400 mg, 1.24 mmol) and 3-amino-N-methylbenzamide (187 mg, 1.24 mmol) in toluene (4 mL, 3 mmoL) was added cesium carbonate (180 mg, 1.86 mmol) and degassed for 15 min. Pd2(dba)3 (56 mg, 0.062 mmol) and BINAP (38 mg, 0.062 mmol) were added and the mixture was heated in the microwave for 30 min at 100° C. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×30 mL) and water (2×30 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure then purified by silica gel column chromatography to provide 3-((3-(3-(4-fluorophenoxy)azetidin-1-yl)phenyl)amino)-N-methylbenzamide (113 mg, 23%) as a solid. Observed mass (M+1): 393.1

Aufarbeitung

  1. customdegassed for 15 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with EtOAc (2×30 mL) and water (2×30 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthen purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a2f5a067739a4df9b9376169031e8e1c
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334269B2

Notizen zur Reaktion

Wird geladen…