Ethyl Acetate → 4-Fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

HRID 1662263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662263
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[C:21]([CH3:28])[N:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[N:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>COCCOC.CCO.O.[Cl-].[Na+].O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].O>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([NH2:18])=[N:9][C:8]2([C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[C:21]([CH3:28])[N:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:33]2[CH:34]=[N:29][CH:30]=[N:31][CH:32]=2)[CH:3]=1

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 585795341-(3-Bromophenyl)-4-fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1H-isoindol-3-amine

Produkt 1

HCID 462027434-Fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amineAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 53485975CID 53485975KatalysatorHCID 962WaterLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittelHCID 86587095Dimethoxyethane ethanol waterLösungsmittel

Versuchsvorschrift

1-(3-Bromophenyl)-4-fluoro-1-(5-methoxy-4,6-dimethylpyridin-2-yl)-1H-isoindol-3-amine (272 mg, 0.62 mmol), pyrimidin-5-ylboronic acid (92 mg, 0.74 mmol), cesium carbonate (604 mg, 1.85 mmol) and dichloro[1,1′-bis (diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (50.4 mg, 0.06 mmol) were dissolved in DME:EtOH:water (6:3:1) (5 mL) and irradiated in a microwave oven for 20 min at 150° C. EtOAc, water and brine were added and the organic phase was collected, dried (Na2SO4) and filtered. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to afford 45 mg (17%) of the title compound.

Aufarbeitung

  1. customirradiated in a microwave oven for 20 min at 150° C
  2. customthe organic phase was collected
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0d0c4774c20a4a5db87b6a5563a1ff12
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030500B2

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