Reaktion #69005

Reaktionsgleichung

1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (2,6-difluoro-pyridin-3-yl)-amide

Lawesson's Reagent

→

5-fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-thiazolo[5,4-b]pyridine

Ausbeute 167.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was capped
2. 2
   Temperaturcooled to room temp
3. 3
   Sonstigepurified by flash column chromatography (0 to 100% EtOAc in hexanes)

Vorschrift

To a suspension of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (2,6-difluoro-pyridin-3-yl)-amide (300 mg, 1.04 mmol) in toluene in a sealable vial was added Lawesson's Reagent (210 mg, 0.52 mmol). The vial was capped and heated to 130° C. for 12 h, cooled to room temp, and loaded directly onto a silica gel column and purified by flash column chromatography (0 to 100% EtOAc in hexanes) to afford 5-fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-thiazolo[5,4-b]pyridine (247 mg, 83% yield). ES MS (M+H+)=285; 1H NMR δ (ppm)(DMSO-d6): 8.99 (1H, d, J=2.23 Hz), 8.64 (1H, s), 8.66-8.53 (1H, m), 7.67 (1H, d, J=3.50 Hz), 7.38 (1H, dd, J=8.74, 1.80 Hz), 6.65 (1H, d, J=3.49 Hz), 3.87 (3H, s).

Quelle