Potassium Phosphate, Tribasic → N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)-2-(pyridin-3-yl)thieno[2,3-b]pyrazine-6-carboxamide

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Reaction Steps

A mixture of 2-chloro-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 68 (100 mg, 0.204 mmol), pyridine-3-boronic acid (37.6 mg, 0.306 mmol), potassium phosphate, tribasic (86 mg, 0.407 mmol), tris(dibenzylideneacetone)dipalladium(0) (9.33 mg, 10.19 μmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (9.71 mg, 0.020 mmol) in butane-2-ol was stirred was stirred at 100° C. for 30 min in microwave. Water was added and extracted with EtOAc. Organic layer was washed with water, brine, dried and evaporated. Crystallization with acetonitrile gave the title compound N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)-2-(pyridin-3-yl)thieno[2,3-b]pyrazine-6-carboxamide 69 (10 mg, 9%). NMR (400 MHz, DMSO-d6) 2.29 (s, 3H), 7.33 (d, J=8.6 Hz, 1H), 7.65 (m, 2H), 7.80 (t, J=7.8 Hz, 1H), 7.92 (d, J=2.0 Hz, 1H), 7.98 (d, J=8.2 Hz, 1H), 8.28 (d, J=7.8 Hz, 1H), 8.32 (s, 1H), 8.61 (s, 1H), 8.63 (t, J=1.6 Hz, 1H), 8.76 (dd, J=4.7 Hz and 1.6 Hz, 1H), 9.43 (d, J=2.0 Hz, 1H), 9.46 (s, 1H), 10.54 (s, 1H), 10.55 (s, 1H). (m/z)=535 (M+H)+.

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