Reaktion #217630

Reaktionsgleichung

4-bromo-2-chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

(4-methyl-2-thienyl)boronic acid

potassium tert-butoxide

(4-methyl-2-thienyl)boronic acid

→

title compound

2-Chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-4-(4-methyl-2-thienyl)benzenesulfonamide

Lösungsmittel

DME

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred in a microwave (set at high absorbance) at 100° C. for a further 30 minutes
2. 2
   SonstigeThe solvent was evaporated after transfer to a new flask with methanol and a few drops of toluene
3. 3
   Wascheneluting with methanol
4. 4
   SonstigeThe appropriate fractions were collected
5. 5
   Sonstigeevaporated in vacuo
6. 6
   Sonstigethe residue purified further by mass

Vorschrift

To a mixture of 4-bromo-2-chloro-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide (E104) (70 mg, 0.14 mmol) and (4-methyl-2-thienyl)boronic acid (40 mg, 0.28 mmol) in DME (3 ml) was added potassium tert-butoxide (142 mg, 1.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. Additional (4-methyl-2-thienyl)boronic acid (20 mg, 0.14 mmol) and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) were then added and the mixture stirred in a microwave (set at high absorbance) at 100° C. for a further 30 minutes. The solvent was evaporated after transfer to a new flask with methanol and a few drops of toluene and the residue passed through an SCX column eluting with methanol followed by 2M ammonia in methanol. The appropriate fractions were collected and evaporated in vacuo and the residue purified further by mass directed autoprep HPLC to afford the title compound (E113). MS (ES+) m/e 506/508 [M+H]+.

Quelle