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tert-butyl 3-(5-chloropyrazin-2-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
69%
With potassium carbonate; In dimethyl sulfoxide; at 80 - 85℃;
A mixture of tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (266 mg, 1.34 mmol), 2,5- dichloropyrazine (260 mg, 1.74 mmol) and K2C03(s) (927 mg, 6.71 mmol) in DMSO (1.5 mL)was stirred for 2 h at 80 °C, then overnight at 85 °C. After cooling to ambient temperature, the mixture was diluted with water and stirred vigorously until the ensuing exotherm dissipated. The aqueous mixture was extracted with Et20, and the biphasic mixture was filtered and separated. The aqueous phase was extracted with DCM, and the Et20 and DCM extracts were combined. The combined organic extracts were dried over anhydrous MgSO4(), filtered, and concentrated in vacuo. The residue was purified by silica chromatography (10percent EtOAc in DCM with 0.05percent NH4OH as the eluent) to cleanly provide the title compound (286 mg, 69percent yield). MS (apci) m/z = 311.0 (M+1); 313.2 (M+2) with Cl pattern.
(6-(6-(tert-butoxycarbonyl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)-5-fluoropyridin-3-yl)boronic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
100%
With potassium carbonate; In 1,4-dioxane; at 80.0℃; for 72.0h;
A solution of <strong>[1366482-40-7](5,6-difluoropyridin-3-yl)boronic acid</strong> (20 mg, 0.13 mmol), tert-butyl3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (50 mg, 0.25 mmol) and K2C03(s) (174 mg, 1.3 mmol) in dioxane (629 tL) was stirred for 3 days at 80C. The reaction mixture was concentrated in vacuo to provide the title compound (20 mg, quantitative yield) of sufficient purity for use without further purification. MS (apci) m/z =338.1 (M+H).
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