Reaktion #660776

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
   SonstigeThe residue was purified by chromatography on silica
5. 5
   Wascheneluting with a gradient of 0-100% ethyl acetate/DCM
6. 6
   Wascheneluting with MeOH (150 mL)
7. 7
   Einengenthe basic methanolic fractions concentrated

Vorschrift

Alternatively, a mixture of ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 72) (6.91 g, 14.11 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (6.22 g, 21.16 mmol), tetrakis(triphenylphosphine)palladium(0) (0.408 g, 0.353 mmol) and potassium carbonate (5.85 g, 42.3 mmol) in 1,4-dioxane (50 mL), DMF (25 mL) and water (12.5 mL) was heated at 100° C. overnight (ca. 20 h). After cooling to RT, the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-100% ethyl acetate/DCM. The resulting material was then passed through an SCX cartridge, eluting with MeOH (150 mL) followed by 2M NH3 in MeOH (250 mL) and the basic methanolic fractions concentrated, to give the title compound (6.276 g).

Quelle