Methyl iodide → Ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate

HRID 1848103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848103
[K].[SH:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=2.I[CH3:18]>CN(C=O)C>[CH3:18][S:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=2

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 178469699HCID 178469699, Verbindung

Produkt 1

HCID 86681077Ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred mixture of ethyl 2-mercaptothiazolo[4,5-b]pyridine-6-carboxylate potassium salt (1.7 g, 6.6 mmol) from the previous step in DMF (10 mL) at 0° C. was added iodomethane (226 μL, 3.6 mmol). After the mixture was stirred at 0° C. for 2 h, it was allowed to warm slowly to rt. The mixture was partitioned between EtOAc (100 mL) and 0.5 M aq Na2CO3 (50 mL). The organic layer was separated and washed with brine (50 mL), dried over Mg2SO4, filtered, and concentrated under reduced pressure to afford ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate (724 mg, 82%) as a yellow solid. The material was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 9.07 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 2.86 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); LCMS (ESI) m/z 255 (M+H)+.

Aufarbeitung

  1. temperatureto warm slowly to rt
  2. customThe mixture was partitioned between EtOAc (100 mL) and 0.5 M aq Na2CO3 (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5794925101be4877a64e786ce04ea489
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952058B2

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