تفاعل #307787

معادلة التفاعل

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

4-(cyanomethyl)benzene boronic acid

potassium carbonate

→

title compound

المردود 72.0%

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

المردود 72.0%

المذيبات

N,N-dimethylacetamide

water

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصextract with DCM (3×20 mL)
2. 2
   تركيزconcentrate
3. 3
   أخرىpurify
4. 4
   غسيل(silica gel chromatography, eluting with 0:100 to 5:95 methanol:DCM)
5. 5
   أخرىDry in a vacuum oven over night
6. 6
   workup.DISSOLUTIONdissolve the yellow oil in acetonitrile
7. 7
   workup.ADDITIONAdd 2 M aq. HCl and water

الإجراء التجريبي

Stir together 3′-chloro-4-(5-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (177 mg, 0.480 mmol), 4-(cyanomethyl)benzene boronic acid (93 mg, 0.576 mmol), potassium carbonate (159 mg, 1.15 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.003 g, 0.003 mmol) and water (1 mL), in N,N-dimethylacetamide (2 mL) at room temperature under nitrogen, then heat at 120° C. for 4 hr. Cool to room temperature, dilute with water (5 mL) and extract with DCM (3×20 mL). Pass the combined DCM extracts through an IST Phase Separator Frit®, concentrate and purify (silica gel chromatography, eluting with 0:100 to 5:95 methanol:DCM). Dry in a vacuum oven over night, then dissolve the yellow oil in acetonitrile. Add 2 M aq. HCl and water then lyophilize to give the title compound as a dark yellow powder (168 mg, 72%). MS (ES): m/z=450.2 [M+H].

المصدر