Reaktion #660765

Reaktionsgleichung

ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

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

potassium carbonate

→

title compound

Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

Lösungsmittel

1,4-dioxane

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to RT
2. 2
   Filtrationfiltered through celite
3. 3
   Einengenthe filtrate was concentrated
4. 4
   SonstigeThe residue was purified by normal phase chromatography
5. 5
   Wascheneluting with a gradient of 0-100% ethyl acetate in cyclohexane

Vorschrift

A mixture of ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (Description 63) (350 mg, 0.695 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (221 mg, 0.751 mmol), tetrakis(triphenylphosphine)palladium(0) (40.1 mg, 0.035 mmol) and potassium carbonate (288 mg, 2.084 mmol) in 1,4-dioxane (1.5 mL), DMF (1.5 mL) and water (0.5 mL) was heated at 100° C. overnight (ca. 16 h). The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-100% ethyl acetate in cyclohexane, to give the title compound (150 mg). LCMS (A) m/z: 491 [M+1]+, Rt 1.20 min (acidic).

Quelle