Reaktion #660866

Reaktionsgleichung

N-[2-bromo-6-methyl-3-(3-methylphenyl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide

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

sodium carbonate

→

title compound

3-Chloro-N-[6-methyl-3-(3-methylphenyl)-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed under a nitrogen atmosphere for ca. 10 min
2. 2
   SonstigeThe reaction mixture was then partitioned between ethyl acetate and water (ca. 30 mL each)
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   Extraktionre-extracted with ethyl acetate (ca. 25 mL)
5. 5
   Sonstigethe solvent removed in vacuo
6. 6
   SonstigePurification by chromatography on silica
7. 7
   Wascheneluting with a gradient of 0-80% ethyl acetate in cyclohexane

Vorschrift

A suspension of N-[2-bromo-6-methyl-3-(3-methylphenyl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide (Description 60) (214 mg, 0.421 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (124 mg, 0.421 mmol), tetrakis(triphenylphosphine)palladium(0) (48.7 mg, 0.042 mmol) and aqueous sodium carbonate (2M) (0.421 mL, 0.843 mmol) was degassed under a nitrogen atmosphere for ca. 10 min before being subjected to microwave heating at 120° C. for 30 min. The reaction mixture was then partitioned between ethyl acetate and water (ca. 30 mL each). The aqueous layer was separated and re-extracted with ethyl acetate (ca. 25 mL) and the combined organic layer passed through a phase separator and the solvent removed in vacuo. Purification by chromatography on silica, eluting with a gradient of 0-80% ethyl acetate in cyclohexane, afforded the title compound (75 mg). LCMS (A) m/z: 495 [M+1]+, Rt 1.31 min (acidic).

Quelle