反应 #307757

反应方程式

4-(hydroxymethyl)benzeneboronic acid

3′-chloro-4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl

potassium carbonate

→

title compound

{4-[4-(1,3,5-Trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl]-phenyl}-methanol hydrochloride

溶剂

N,N-dimethylacetamide

water

反应条件

后处理

1. 1
   温度Cool to room temperature
2. 2
   其他purify
3. 3
   其他further purify
4. 4
   洗涤eluting with (5:95 to 20:80 methanol:DCM)
5. 5
   workup.DISSOLUTIONDissolve in acetonitrile
6. 6
   workup.ADDITIONadd 2 M aq. HCl and water

实验过程

Stir together 4-(hydroxymethyl)benzeneboronic acid (182 mg, 1.2 mmol), 3′-chloro-4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (321 mg, 1.0 mmol), potassium carbonate (332 mg, 2.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 5 μmol) in dry N,N-dimethylacetamide (4 mL) and water (2 mL) at room temperature. Heat to 120° C. for 6 hr. under nitrogen. Cool to room temperature, purify using SCX chromatography and further purify using silica gel chromatography eluting with (5:95 to 20:80 methanol:DCM). Dissolve in acetonitrile, and add 2 M aq. HCl and water then lyophilize to give the title compound as a peach coloured powder (405 mg, 94%). MS (ES): m/z=393 [M+H].

来源