Reaktion #660775

Reaktionsgleichung

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

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

potassium carbonate

→

title compound

Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-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
   SonstigePurification by chromatography on silica
5. 5
   Wascheneluting with a gradient of 0-100% ethyl acetate in DCM

Vorschrift

A mixture of ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 72) (402 mg, 0.82 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (483 mg, 1.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (47.4 mg, 0.041 mmol) and potassium carbonate (340 mg, 2.46 mmol) in 1,4-dioxane (3 mL), DMF (1.5 mL) and water (0.75 mL) was heated at 110° C. for ca. 2 h. After cooling to RT, the reaction mixture was filtered through celite and the filtrate was concentrated. Purification by chromatography on silica, eluting with a gradient of 0-100% ethyl acetate in DCM, afforded the title compound (355 mg). LCMS (A) m/z: 477 [M+1]+, Rt 1.18 min (acidic).

Quelle