Tributylvinyltin → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-vinylthieno[2,3-b]pyrazine-6-carboxamide

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A solution of 7-bromo-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 42 (22 mg, 0.041 mmol), bis(triphenylphosphine)palladium(II) chloride (1.445 mg, 2.058 μmol) and tributyl(vinyl)tin (0.024 mL, 0.082 mmol) in toluene (1 mL) was stirred for 30 min at 110° C. in microwave. After filtration, diluted with toluene and washed with water, brine, dried and evaporated. Purification by HPLC gave the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-vinylthieno[2,3-b]pyrazine-6-carboxamide 43c (2 mg, 10.09%). NMR (400 MHz, DMSO-d6) 2.27 (s, 3H), 5.76 (dd, J=12.0 and 2.3 Hz, 1H), 8.85-8.91 (dd, J=17.6 and 1.9 Hz, 1H), 7.28-7.38 (m, 2H), 7.58-7.68 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.91 (d, J=1.9 Hz, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.05 (t, J=1.9 Hz, 1H), 8.80 (d, J=2.3, 1H), 8.94 (d, J=2.3 Hz, 1H), 10.37 (s, 1H), 10.38 (s, 1H). (m/z)=482 (M+H)+.

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