反応 #53443

反応方程式

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

収率 47.0%

反応条件

後処理

1. 1
   ろ過filtered through a pad of celite
2. 2
   その他The residue is purified
3. 3
   その他to give a pale yellow oil that
4. 4
   その他crystallized from EtOH/Et2O
5. 5
   その他to give a pale yellow solid

実験手順

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.

出典