Dimethylformamide → 4-Fluoro-1-(2-fluoro-5-(pyrimidin-5-yl)phenyl)-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine

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Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH: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:7]=1.[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>[Cl-].[Na+].O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[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:6]1[CH:7]=[C:2]([C:31]2[CH:32]=[N:27][CH:28]=[N:29][CH:30]=2)[CH:3]=[CH:4][C:5]=1[F:26])[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

1-(5-Bromo-2-fluorophenyl)-4-fluoro-1-(2-methylpyridin-4-yl)-1H-isoindol-3-amine (80 mg, 0.19 mmol), 5-pyrimidinylboronic acid (31.1 mg, 0.25 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (15.77 mg, 0.02 mmol), potassium carbonate (2.5 M, aq, 0.290 mL, 0.58 mmol) and DMF (2 mL) were added to a vial and heated in a microwave reactor at 150° C. for 15 min. Brine was added and the product mixture was extracted EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification by preparative HPLC afforded 34.0 mg (43% yield) of the title compound.

Aufarbeitung

extractionthe product mixture was extracted EtOAc
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-b57761e9d39146669859980376aeba9b
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08030500B2

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