Reaktion #660770

Reaktionsgleichung

ethyl 2-bromo-6-methyl-4-[(phenylsulfonyl)amino]thieno[2,3-b]pyridine-5-carboxylate

1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid

potassium carbonate

→

title compound

Ethyl 6-methyl-4-[(phenylsulfonyl)amino]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

Lösungsmittel

1,4-dioxane

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to RT
2. 2
   Filtrationthe reaction mixture was filtered through celite
3. 3
   Einengenthe filtrate was concentrated
4. 4
   SonstigeThe residue was purified via normal phase chromatography
5. 5
   Wascheneluting with 0-100% ethyl acetate in DCM

Vorschrift

A mixture of ethyl 2-bromo-6-methyl-4-[(phenylsulfonyl)amino]thieno[2,3-b]pyridine-5-carboxylate (Description 67) (6.27 g, 13.77 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (8.10 g, 27.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.796 g, 0.688 mmol) and potassium carbonate (5.71 g, 41.3 mmol) in 1,4-dioxane (40 mL), DMF (20 mL) and water (10 mL) was heated at 100° C. for ca. 3.5 h. After cooling to RT, the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified via normal phase chromatography eluting with 0-100% ethyl acetate in DCM, to give the title compound (5.81 g). LCMS (A) m/z: 443 [M+1]+, Rt 1.05 min (acidic).

Quelle