Dimethylformamide → N-[5-(2-Cyano-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide

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Reaktionsgleichung

Br[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])=[N:10][C:9]=2[CH3:24])[CH:5]=[CH:4][N:3]=1.[CH3:25][N:26](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])=[N:10][C:9]=2[CH3:24])[CH:5]=[CH:4][N:3]=1)#[N:26]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A solution of N-[5-(2-Bromo-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide (100 mg, 0.24 mmol), Zn(CN)2 (43.0 mg, 0.36 mmol), and Pd(PPh3)4 (20.0 mg, 0.02 mmol) in DMF (4.0 mL) was degassed by purging with a stream of nitrogen for 10 minutes. The mixture was heated to 110° C. overnight, cooled to room temperature, diluted with CH2Cl2, washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on silica gel to give the title compound (45 mg).

Aufarbeitung

customby purging with a stream of nitrogen for 10 minutes
temperaturecooled to room temperature
additiondiluted with CH2Cl2
washwashed with water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-4cff4c7e3be84091b0f7da8dda9ff6e4
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08455658B2

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