반응 #683125

반응 방정식

3,5-dibromopyrazin-2-amine

(S)—N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

CH2Cl2

Na2CO3

→

(S)-4-(3-amino-6-bromopyrazin-2-yl)-N-(2-hydroxy-1-phenylethyl)benzamide

수율 118.5%

용매

EtOAc

DME

반응 조건

후처리

1. 1
   세척The organic layer was washed with sat NaHCO3, water and brine
2. 2
   건조dried over Na2SO4
3. 3
   여과filtered off
4. 4
   농축concentrated in vacuo
5. 5
   기타The crude product was purified with silica flash chromatography
6. 6
   세척eluting with 0-100% of EtOAc (containing 10% of MeOH) in heptane
7. 7
   기타triturated with ether

실험 절차

To a solution of 3,5-dibromopyrazin-2-amine (826 mg, 3.27 mmol), (S)—N-(2-hydroxy-1-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (600 mg, 1.634 mmol), and PdCl2(dppf).CH2Cl2 adduct (133 mg, 0.163 mmol) in DME (12.3 mL) was added 2 M Na2CO3 (4.08 mL). The reaction mixture was heated at microwave synthesizer (120° C., 10 min). The reaction mixture was worked uup with EtOAc. The organic layer was washed with sat NaHCO3, water and brine, dried over Na2SO4, filtered off, concentrated in vacuo. The crude product was purified with silica flash chromatography eluting with 0-100% of EtOAc (containing 10% of MeOH) in heptane, and triturated with ether to provide 800 mg of (S)-4-(3-amino-6-bromopyrazin-2-yl)-N-(2-hydroxy-1-phenylethyl)benzamide. LCMS (m/z): 415 (MH+), 0.73 min.

출처