Water → 6-({[t-Butyl(dimethyl)silyl]oxy}methyl)nicotinonitrile

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Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[N:6][CH:7]=1.O.[CH3:18][N:19]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Si:10]([O:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:18]#[N:19])=[CH:7][N:6]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A solution of 5-bromo-2-({[t-butyl(dimethyl)silyl]oxy}methyl)pyridine (0.30 g, 1.0 mmol) that was obtained in Example 23 (23a), zinc cyanide (0.18 g, 1.5 mmol), bis(dibenzylideneacetone)palladium (18 mg, 0.02 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (44 mg, 0.08 mmol) in N-methyl-2-pyrrolidinone (4 ml) was stirred at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into water and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:9) as the eluent to afford the title compound (0.23 g) in a yield of 93% as a white crystalline solid.

Aufarbeitung

temperatureAfter cooling to room temperature
extractionextracted with ether
washThe extract was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
filtrationAfter filtration
customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-c563039b8dfd485a8dac4f4967d7e6a6
Quelldatensatz: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07687491B2

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