u2032 t m 267 u00b0 c dsc t g 127 u00b0 c dsc tlc r f 0 30 acetone hexanes 1 4 1 h nmr 400 mhz cdcl 3 u03b4 3 70 s 12h 5 84 d j 8 0 2h 6 25 s 2h 6 32 d j 8 0 2h 6 43 dd j 8 0 2 4 2h 6 62 6 88 m 24h 7 14 dd j 8 0 1 6 2h 7 42 7 45 m 3h 13 c nmr 100 mhz cdcl 3 u03b4 55 28 113 92 114 42 116 68 120 45 124 58 125 20 126 27 126 88 127 91 129 04 130 60 131 20 132 15 133 37 135 64 135 86 139 95 140 55 146 73 149 90 155 45 hr ms calcd for c 61 h 49 n 3 o 4 887 3723 found 887 3683 a mixture of chemical formula iii 6 u2032 2 50 g 5 0 mmol 3 cyanophenyl boronic acid 1 628 g 11 0 mmol pd pph 3 4 350 mg 0 30 mmol and sodium carbonate 2 70 g 25 mmol in dme 50 ml and distilled water 10 ml was refluxed for 24 h under argon the mixture was then extracted with ch 2 cl 2 the combined organic extracts were dried over anhydrous mgso 4 and concentrated by rotary evaporation the crude product was purified by column chromatography on silica gel using 1 1 ch 2 cl 2.