Реакция #40555

Уравнение реакции

6-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid

2,4-di-chloropyrimidine

potassium fluoride

→

6-(2-Chloropyrimidin-4-yl)-4-[6-tri-fluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеdegassed with argon for 10 minutes
2. 2
   workup.ADDITIONTri-tert-butyl-phosphonium tetrafluoroborate is added
3. 3
   ДругоеThe solvent is removed in a rotary evaporator
4. 4
   workup.DISSOLUTIONthe residue is dissolved in DMF
5. 5
   Другоеthe crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

Методика

6-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid, 2,4-di-chloropyrimidine, potassium fluoride and tris(dibenzylideneacetone)dipalladium(0) are dissolved in dry THF and degassed with argon for 10 minutes. Tri-tert-butyl-phosphonium tetrafluoroborate is added, and the reaction mixture is stirred at room temperature for 16 hours. LC-MS analysis shows complete conversion. The solvent is removed in a rotary evaporator, the residue is dissolved in DMF and the crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid)). MS (ES+) m/z 653 (M+H).

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