Br[C:2]1[S:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH3:11][C:12]1(C)[C:16](C)(C)OB(CC=C)O1.C(=O)([O-])[O-].[K+].[K+]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].CN(C=O)C>[CH2:16]([C:2]1[S:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1)[CH:12]=[CH2:11]In a 15 mL microwave reaction vial was added 2-bromothieno[2,3-c]furan-6(4H)-one (45 mg, 0.205 mmol), 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane (34.5 mg, 0.205 mmol, 1.0 eq), potassium carbonate (56.8 mg, 0.411 mmol, 2.0 eq) and palladium triphenylphosphane (1:4) (23.7 mg, 0.021 mmol, 0.1 eq). To above mixture was added DMF (1.0 mL), de-gas and filled with N2. The vial was heated to 100° C. for 60 min, cooled down, diluted with EtOAc, washed with aqueous sodium bicarbonate, brine and water. The organic phase was dried over anhydrous Na2SO4, filtered, concentrated. The crude product was purified by flash column chromatography. LC-MS (IE, m/z): 181.2 [M+1]+.
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