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0 °C

To a solution of tert-butyl 2-chloro-4H-thieno[3,2-b]pyrrole-4-carboxylate (0.52 g, 2 mmol) and B(OiPr)3 (0.7 mL, 3 mmol) in 10 mL of THF cooled at 0° C. was added a LDA solution (4 mmol, prepared from 0.56 mL of iPr2NH, 5.84 mL of THF and 1.6 mL of 2.5 M n-BuLi solution in hexane) by a syringe pump over a period of 2 h. The reaction mixture was stirred for additional 6 h at 0° C. before being quenched by addition of 20 mL of saturated NH4Cl solution. The product was extracted with 2×20 mL of EtOAc, dried over Na2SO4, filtered and concentrated. The residue was purified by Combiflash on a silica gel column eluted with a gradient of up to 60% EtOAc/hexanes to give 0.3 g of the title compound as a solid.

1. custombefore being quenched by addition of 20 mL of saturated NH4Cl solution
2. extractionThe product was extracted with 2×20 mL of EtOAc
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by Combiflash on a silica gel column
7. washeluted with a gradient of up to 60% EtOAc/hexanes