Реакция #69583

Уравнение реакции

H2O

HBTU

DIPEA

1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

4-bromo-2-pyridinecarboxylic acid

HOBT

→

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

Выход 52.6%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe DMF was evaporated under vacuo
2. 2
   workup.ADDITION10 ml of DCM were added
3. 3
   Промывкаwashed with 2M aq. HCl solution (10 ml) saturated aq. NaHCO3 solution (10 ml) and brine (10 ml)
4. 4
   Другоеdried on a phase separation cartridge
5. 5
   Другоеevaporated in vacuo
6. 6
   ДругоеThe crude material was purified by silica chromatography
7. 7
   ДругоеThe desired fractions were then collected
8. 8
   Концентрированиеconcentrated to dryness

Методика

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (200 mg, 0.680 mmol) in DMF (10 ml) was added 4-bromo-2-pyridinecarboxylic acid (137 mg, 0.680 mmol), HOBT.H2O (104 mg, 0.680 mmol), HBTU (258 mg, 0.680 mmol) and DIPEA (0.356 ml, 2.039 mmol) and the reaction mixture was stirred at room temperature for 2.5 hours. The DMF was evaporated under vacuo then 10 ml of DCM were added and washed with 2M aq. HCl solution (10 ml) saturated aq. NaHCO3 solution (10 ml) and brine (10 ml), dried on a phase separation cartridge and evaporated in vacuo. The crude material was purified by silica chromatography using a gradient isohexane/EtOAc [100/0] to [50/50] then to [0/100]). The desired fractions were then collected and concentrated to dryness to give 1-[(4-bromo-2-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (171 mg, 0.358 mmol, 52.6% yield).

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