1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin

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Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[N:6][CH:7]=1.[C:24]([Si:28](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:27])([CH3:26])[CH3:25].C([O:48][CH2:49][CH3:50])C.[F-].[K+].Cl[CH2:54]CCl>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>[C:12]([O:11][C:9]([N:8]([C:5]1[C:4]([CH3:23])=[CH:3][C:2]([C:49]([CH3:50])([CH3:54])[O:48][SiH2:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:7][N:6]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of 5-bromo-2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-pyridin (26.0 g, 67.1 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (47.6 g, 109 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.90 g, 1.42 mmol) in 1,2-dichloroethane (80 mL) was stirred at 90° C. for two days. The mixture was cooled to 0° C. and diethyl ether (200 mL) was added followed by saturated aqueous potassium fluoride (40 mL). The mixture was stirred vigourously for 30 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 100:0→95:5) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin (18.0 g, 59%).

Aufarbeitung

filtrationfiltered
washThe organic phase was washed with water
customdried
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-36d991e903c24644903420e72332da4d
Quelldatensatz: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07071175B1

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