Methyl iodide → 1-(4-Methyl-5-methylsulfanyl-3-pyridin-3-yl-thiophen-2-yl)-propan-1-one

HRID 478184

Reaktionsgleichung

O=[C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]#N.[C:12](=[S:14])=[S:13].Br[CH2:16][C:17](=[O:20])[CH2:18][CH3:19].[CH3:21]I.[NH4+].[Cl-]>CN(C=O)C>[CH3:4][C:3]1[C:2]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[C:16]([C:17](=[O:20])[CH2:18][CH3:19])[S:13][C:12]=1[S:14][CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 3-oxo-3-pyridin-3-yl-propionitrile (11.9 mmol) in DMF (100 mL) was added CS2 (0.90 ml, 15.0 mmol) at 0° C. The reaction was stirred at 0° C. for 45 minutes under nitrogen then 1-bromo-butan-2-one (1.79 g, 11.8 mmol) was added via a syringe at 0° C. The reaction was stirred for another 30 minutes then methyl iodide (1.69 g, 11.8 mmol) was added via syringe at 0° C. The resulting mixture was stirred for another 30 minutes then warmed to ambient temperature and poured into saturated aqueous NH4Cl solution (300 mL). The solution was extracted with ethyl acetate (200 mL×3) and the combined organic layers were dried over Na2SO4 then concentrated in vacuo. Purification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate) afforded 1.05 g desired product. 1H NMR (CDCl3): δ8.8(d, 1H), 8.6 (s, 1H), 7.8 (d, 1H), 7.5 (dd, 1H),2.8 (s, 3H), 2.3 (q, 2H), 1.0 (t, 3H).

Aufarbeitung

stirringThe reaction was stirred for another 30 minutes
stirringThe resulting mixture was stirred for another 30 minutes
temperaturethen warmed to ambient temperature
extractionThe solution was extracted with ethyl acetate (200 mL×3)
dry with materialthe combined organic layers were dried over Na2SO4
concentrationthen concentrated in vacuo
customPurification by chromatography (Silica Gel, 3:1 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-d3b1d6e25bde40b5a2a965a981b9bb06
Quelldatensatz: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06642227B2

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