反应详情

温度

120 °C

To a solution of cis-(5-bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.095 g, 0.29 mmol) in DME (2 mL) was added N′N′-dimethylethylenediamine (0.005 g), pyrazole (0.039 g, 0.58 mmol), copper iodide (0.011 g) and potassium carbonate (0.040 g, 0.29 mmol). The reaction mixture was placed under nitrogen then sealed in a vial and heated at 120° C. for 79 hours. The solution was partitioned between DCM and water and the phases separated using a hydrophobic frit. The organic phase was evaporated and the compound was purified by chromatography on a silica cartridge eluting 0-10% methanol in DCM then re-purified on a larger cartridge using 0-3% methanol in DCM. The compound was further purified by HPLC on a C6 phenyl column, eluting with 50%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were evaporated to give the title compound as a colourless oil (0.02 g). LCMS m/z 316.19 [M+H]+ R.T.=10.74 min (Analytical Method 2).

1. customthen sealed in a vial and
2. customThe solution was partitioned between DCM and water
3. customthe phases separated
4. customThe organic phase was evaporated
5. customthe compound was purified by chromatography on a silica cartridge
6. washeluting 0-10% methanol in DCM
7. customthen re-purified on a larger cartridge
8. customThe compound was further purified by HPLC on a C6 phenyl column
9. washeluting with 50%-98% acetonitrile in water (0.1% formic acid)
10. additionThe fractions containing the desired product
11. customwere evaporated