Реакция #53443

Уравнение реакции

N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide

DMF

d-tartaric acid

→

N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-cyanopyrrolo[1,2-a]pyrazine-3-carboxamide Tartrate

Выход 47.0%

Условия реакции

Обработка

1. 1
   Фильтрацияfiltered through a pad of celite
2. 2
   ДругоеThe residue is purified
3. 3
   Другоеto give a pale yellow oil that
4. 4
   Другоеcrystallized from EtOH/Et2O
5. 5
   Другоеto give a pale yellow solid

Методика

To an argon sparged solution of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide (0.77 g, 2.14 mmol) in DMF (25 mL) is added zinc cyanide (0.26 g, 2.20 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.25 g, 0.21 mmol). The resulting suspension is stirred at 95° C. for 48 h, then filtered through a pad of celite. The residue is purified using preparative chromatography (carried out on a Chiral OD column using a 40% IPA/heptanes each containing 0.1% diethylamine) to give a pale yellow oil that is salted with d-tartaric acid and crystallized from EtOH/Et2O to give a pale yellow solid. Yield 47%. HRMS (FAB) calcd for C16H17N5O+H 296.1511, found 296.1520.

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