Sodium Carbonate → HCID 57448381, Verbindung

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Reaktionsgleichung

[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:18]1[S:19][C:20]2[C:21]([N:26]=1)=[N:22][CH:23]=[CH:24][CH:25]=2.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[S:19]1[C:20]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[N:26]=[C:18]1[O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 4-hydroxyphenethyl alcohol (1.16 g, 8.4 mmol, 1.2 equiv.) and K2CO3 (1.94 g, 14.06 mmol, 2 equiv.) in CH3CN (12 mL) was added 2-chloro[1,3]thiazolo[4,5-b]pyridine (1.2 g, 7.03 mmol, 1 equiv.). The reaction mixture was heated to 80° C. and stirred for 16 h. Satd. aq. Na2CO3 (25 mL) was added to the reaction mixture, which was then extracted with isopropyl acetate (2×30 mL). The combined organic layers were dried, filtered, and concentrated. The crude material was purified by column chromatography (50% EtOAc/hexanes-100% EtOAc), which afforded the title compound as a light orange oil (74%). MS (ESI): mass calcd. for C14H12N2O2S, 272.32; m/z found, 273.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.56 (dd, J=4.8, 1.6, 1H), 8.03 (dd, J=7.9, 1.7, 1H), 7.37-7.29 (m, 4H), 7.22 (dd, J=7.9, 4.8, 1H), 3.88 (dd, J=12.5, 6.5, 2H), 2.91 (t, J=6.6, 2H), 2.03 (t, J=5.9, 1H).

Aufarbeitung

extractionwas then extracted with isopropyl acetate (2×30 mL)
customThe combined organic layers were dried
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by column chromatography (50% EtOAc/hexanes-100% EtOAc), which

Quellen und Nachweise

ORD-Eintrag: ord-af239343418a458eb459e8643edc95f7
Quelldatensatz: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07939527B2

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