Cesium carbonate → [6-(Thiazolo[4,5-b]pyridin-2-yloxy)-furo[3,2-b]pyridin-2-yl]-methanol

HRID 1947505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947505
[OH:1][CH2:2][C:3]1[O:11][C:10]2[C:5](=[N:6][CH:7]=[C:8]([OH:12])[CH:9]=2)[CH:4]=1.Cl.Cl[C:15]1[S:16][C:17]2[C:18]([N:23]=1)=[N:19][CH:20]=[CH:21][CH:22]=2.C([O-])([O-])=O.[Cs+].[Cs+].[NH4+].[Cl-]>CN(C=O)C>[S:16]1[C:17]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:23]=[C:15]1[O:12][C:8]1[CH:9]=[C:10]2[O:11][C:3]([CH2:2][OH:1])=[CH:4][C:5]2=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 467379422-(Hydroxymethyl)furo[3,2-b]pyridin-6-olHCID 574827652-Chlorothiazolo[4,5-b]pyridine hydrochloride

Produkt 1

HCID 59577380[6-(Thiazolo[4,5-b]pyridin-2-yloxy)-furo[3,2-b]pyridin-2-yl]-methanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-(hydroxymethyl)furo[3,2-b]pyridin-6-ol (200 mg, 1.21 mmol), 2-chloro-thiazolo-[4,5-b]pyridine hydrochloride (300 mg, 1.45 mmol) and Cs2CO3 (800 mg, 2.46 mmol) was added DMF (12 mL). The suspension was stirred (rt, 16 h) and then poured into ice-cold sat'd. aq. NH4Cl. The resultant precipitate was filtered, rinsed with water and dried to provide the product as a beige solid (326 mg, 90%). MS (ESI): mass calcd. for C14H9N3O3S, 299.04; m/z found, 300.0 [M+H]+. 1H NMR (600 MHz, CD3OD): 8.63 (d, J=2.3, 1H), 8.49 (dd, J=4.9, 1.6, 1H), 8.36 (dd, J=8.0, 1.6, 1H), 8.23 (dd, J=2.3, 0.9, 1H), 7.37 (dd, J=8.0, 4.9, 1H), 6.95 (s, 1H), 4.76 (s, 2H).

Aufarbeitung

  1. additionpoured into ice-cold sat'd
  2. filtrationThe resultant precipitate was filtered
  3. washrinsed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e9154aec56a04bb495ba00a339867fa8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399465B2

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