تفاعل #307764

معادلة التفاعل

water

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

potassium carbonate

(4-Cyanomethylphenyl)boronic acid

→

title compound

المردود 52.0%

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

المردود 52.0%

المذيبات

N,N-dimethylacetamide

ظروف التفاعل

المعالجة

1. 1
   أخرىreaction for 6 hr
2. 2
   غسيلAdd DCM and wash with water
3. 3
   أخرىDry
4. 4
   أخرىpurify (silica gel chromatography
5. 5
   غسيلeluting with 50:50 to 100:0 ethyl acetate

الإجراء التجريبي

Combine 3′-chloro-4-(1-ethyl-5-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.300 g, 0.935 mmol), potassium carbonate (0.310 g, 2.24 mmol), (4-Cyanomethylphenyl)boronic acid (0.180 g, 1.12 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.011 g, 0.009 mmol) in N,N-dimethylacetamide (1.9 mL). Add water (940 μL), and reflux reaction for 6 hr. Continue to heat at 70° C. for 18 hr. Add DCM and wash with water. Extract water layer three times with DCM. Dry combined organics (magnesium sulfate) and purify (silica gel chromatography, eluting with 50:50 to 100:0 ethyl acetate:hexanes then 10:90 to 20:80 methanol:ethyl acetate), to give the free base of the title compound (196 mg, 52%). Dissolve the free base (0.194 g, 0.482 mmol) in acetonitrile (579 μL) and add aq. 1 N HCl solution (579 μL, 0.579 mmol). Shake for 15 min. at ambient temperature. Freeze dry to give the title compound (201 mg, 95%). MS (ES): m/z=402 [M+H]+.

المصدر