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

Participants

Reaction Conditions

Reaction Steps

A mixture of 24 (30 mg, 0.061 mmol), pyridine-3-boronic acid (11.2 mg, 0.092 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.8 mg, 3.06 μmol), potassium phosphate, tribasic (26 mg, 0.122 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (2.92 mg, 6.12 μmol) in butanol-2-ol was stirred at 100° C. for 30 min. Diluted with EtOAc and washed with water, brine, dried and evaporated. Triturating with acetonitrile gave the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-(pyridin-3-yl)thieno[2,3-b]pyrazine-6-carboxamide 25h (9 mg, 27.6%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.29 (s, 3H), 7.33 (d, J=8.2 Hz, 1H), 7.58-7.69 (m, 3H), 7.76 (d, J=7.8 Hz, 1H), 7.90 (s, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 8.62 (m, 2H), 8.76 (d, J=4.7 Hz, 1H), 9.45 (m, 2H), 10.38 (s, 1H), 10.55 (s, 1H). (m/z)=533 (M+H)+.

Provenance & Evidence