反应详情

温度

80 °C

A mixture of 4-(tert-butoxycarbonyl)-2-chloro-4H-thieno[3,2-b]pyrrol-5-ylboronic acid (200 mg, 0.66 mmol), N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine (160 mg, 0.61 mmol, provided by Chemzon Scientific Inc, Montreal, Canada), Pd(dppf)2Cl2CH2Cl2 (18 mg) and K3PO4 (260 mg) in a 20 mL sealed-tube flask was vented 4 times with nitrogen. 1,4-Dioxane (3 mL and water (0.4 mL) were introduced by syringes and the mixture was vented twice with nitrogen. The reaction mixture was heated at 80° C. for 1 h and TLC showed no starting materials were left. After being cooled to r.t., the reaction mixture was treated with 3 mL of 1N HCl, and stirred for 3 h. The mixture was then extracted with 20 mL of EtOAc, and the extract was dried over Na2SO4, filtered through a pad of silica gel. The filtrate was concentrated under vacuum and the residue was purified by Combiflash on a silica gel column eluted with a gradient of up to 60% EtOAc/hexanes to give 11 mg of the title compound as a solid.

1. waitwere left
2. temperatureAfter being cooled to r.t.
3. extractionThe mixture was then extracted with 20 mL of EtOAc
4. dry with materialthe extract was dried over Na2SO4
5. filtrationfiltered through a pad of silica gel
6. concentrationThe filtrate was concentrated under vacuum
7. customthe residue was purified by Combiflash on a silica gel column
8. washeluted with a gradient of up to 60% EtOAc/hexanes