Reaktion #88383

Reaktionsgleichung

acetic acid

propane-1-sulfonic acid {3-[1-(2,6-dichloro-benzoyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide

2-(4-bromo-pyrazol-1-yl)-pyrimidine

potassium carbonate

→

desired compound

propane-1-sulfonic acid {2,4-difluoro-3-[5-(1-pyrimidin-2-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture is microwave irradiated at 145° C. for 15 minutes
2. 2
   Extraktionextracted with 2×1 mL of ethyl acetate
3. 3
   EinengenThe combined organic layer is concentrated under vacuum
4. 4
   workup.DISSOLUTIONthe residue dissolved in 500 μL of dimethylsulfoxide
5. 5
   Sonstigepurified by HPLC
6. 6
   Wascheneluting with water/acetonitrile and 0.1% trifluoroacetic acid, 20-100% acetonitrile at 6 mL per minute
7. 7
   Einengenconcentrated under vacuum

Vorschrift

To a solution of propane-1-sulfonic acid {3-[1-(2,6-dichloro-benzoyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide (32, 18 mg, 0.026 mmol) and 2-(4-bromo-pyrazol-1-yl)-pyrimidine (33, 4.95 mg, 0.022 mmol) in 800 μL of acetonitrile is added 400 μL of 1M aqueous potassium carbonate and approximately 1-2 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium (II) (PdCl2 dppf). The reaction mixture is microwave irradiated at 145° C. for 15 minutes, then neutralized with acetic acid, and extracted with 2×1 mL of ethyl acetate. The combined organic layer is concentrated under vacuum, the residue dissolved in 500 μL of dimethylsulfoxide and purified by HPLC using a C18 column, eluting with water/acetonitrile and 0.1% trifluoroacetic acid, 20-100% acetonitrile at 6 mL per minute. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=524.5.

Quelle