Реакция #69587

Уравнение реакции

1-[(4-bromo-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

sodium carbonate

1,2-dimethoxyethane

→

title compound

Выход 1.3%

2′-[(4-{[4-(Trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2,4′-bipyridine

Выход 1.3%

Растворители

ethanol

water

EtOH

Условия реакции

Обработка

1. 1
   Фильтрацияfiltered through celite
2. 2
   КонцентрированиеThe filtrate was concentrated in vacuo
3. 3
   workup.ADDITIONthen diluted with MeOH
4. 4
   Фильтрацияfiltered through an SCX cartridge (1 g)
5. 5
   Промывкаwash so product
6. 6
   Концентрированиеconcentrated
7. 7
   workup.ADDITIONdiluted with MeOH
8. 8
   Фильтрацияfiltered through a 5 g SCX column (washed with MeOH, eluted with NH3 0.5M in MeOH)
9. 9
   КонцентрированиеThe eluted product was concentrated in vacuo
10. 10
    workup.DISSOLUTIONthen dissolved in MeCN/DMSO 1:1
11. 11
    Другоеpurified by MDAP
12. 12
    Концентрированиеconcentrated under vacuo

Методика

In a 5 ml microwave vial were added 1-[(4-bromo-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 17) (150 mg, 0.314 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Description 5) (129 mg, 0.627 mmol), bis(triphenylphosphine)palladium(II) chloride (44.0 mg, 0.063 mmol), sodium carbonate (100 mg, 0.941 mmol), 1,2-dimethoxyethane (1.5 ml), ethanol (1.0 ml) and water (0.50 ml). The reaction mixture was heated for 20 minutes at 120° C. in the microwave. The crude material was diluted in EtOH and filtered through celite. The filtrate was concentrated in vacuo then diluted with MeOH and filtered through an SCX cartridge (1 g). All material came out with MeOH wash so product concentrated, diluted with MeOH and filtered through a 5 g SCX column (washed with MeOH, eluted with NH3 0.5M in MeOH). The eluted product was concentrated in vacuo then dissolved in MeCN/DMSO 1:1 and purified by MDAP. The desired fractions were combined and concentrated under vacuo to give the title compound (2 mg).

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