Tetramethyltin → (R,R)-N-[3-(4-ethoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide

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Reaktionsgleichung

[Sn](C)(C)(C)[CH3:2].Br[C:7]1[C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)=[N:9][S:10][C:11]=1[NH:12][C:13]([C@@H:15]1[CH2:17][C@H:16]1[CH3:18])=[O:14]>CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:8]2[C:7]([CH3:2])=[C:11]([NH:12][C:13]([C@@H:15]3[CH2:17][C@H:16]3[CH3:18])=[O:14])[S:10][N:9]=2)=[CH:20][CH:21]=1)[CH3:27]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

Add PdCl2(PPh3)2 (0.07 g, 0.09 mmol) and Sn(CH3)4 (0.34 mL, 0.44 g, 2.48 mmol) to (R,R)—N-[4-bromo-3-(4-ethoxyphenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide (0.24 g, 0.62 mmol) in DMF (1 mL) and stir the reaction mixture at 130° C. in a sealed tube overnight. Dilute with EtOAc (100 mL) and brine (100 mL). Collect the organic phase, dry (MgSO4), and evaporate. Filter over silica gel and wash with EtOAc. Evaporate and crystallize from EtOAc/hexane to afford (R,R)—N-[3-(4-ethoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide. Yield: 81.7%.

Aufarbeitung

customCollect the organic phase
dry with materialdry (MgSO4)
customevaporate
filtrationFilter over silica gel
washwash with EtOAc
customEvaporate
customcrystallize from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag: ord-b6d5b3ed8e984b179def2ad63ebc345b
Quelldatensatz: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07960419B2

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