反应 #73800

反应方程式

[2-(4-Bromo-phenyl)-2-(4-hydroxy-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester

2-chloropyrazine

K2CO3

→

desired product

收率 68.8%

{2-(4-Bromo-phenyl)-2-[4-(pyrazin-2-yloxy)-phenyl]-ethyl}-methyl-amine

收率 68.8%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   温度Upon cooling
2. 2
   其他the solvent was removed under reduced pressure
3. 3
   其他the residue was partitioned between ethyl acetate and saturated NaHCO3 solution
4. 4
   干燥The organic layer was dried (MgSO4)
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   workup.ADDITIONThe crude product was then treated with saturated HCl in diethyl ether (15 ml)
8. 8
   其他The solvent was then removed under reduced pressure
9. 9
   其他the crude product was purified by Phenomenex_Strata_SCX column chromatography
10. 10
    洗涤eluting with methanol

实验过程

A solution of [2-(4-Bromo-phenyl)-2-(4-hydroxy-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (125 mg, 0.31 mmol), 2-chloropyrazine (35.2 mg, 0.31 mmol) and K2CO3 (213 mg, 1.54 mmol) in dimethylformamide (8 ml) was heated to 100° C. for 17 hours. Upon cooling, the solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was then treated with saturated HCl in diethyl ether (15 ml) and stirred at room temperature for 72 hours. The solvent was then removed under reduced pressure and the crude product was purified by Phenomenex_Strata_SCX column chromatography eluting with methanol followed by 2N ammonia in methanol to afford the desired product (82 mg). LC/MS: (PS-B3) Rt 3.17 [M+H]+ 384.

来源