Potassium Phosphate, Tribasic → HCID 67125562, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 95 (204 mmol, 100 mg), pyridine-3-boronic acid (0.306 mmol, 37 mg), potassium phosphate, tribasic (0.408, 87 mg), (0.05 eq, 9 mg), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.1 eq, 9 mg) was stirred at 100° C. for 30 min. Evaporated to dryness and purified by chromatography (0-100% ethyl acetate in CH2Cl2) and HPLC to yield N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(pyridin-3-yl)thieno[2,3-b]pyrazine-6-carboxamide 96j (3 mg, 2%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.29 (s, 3H), 7.32 (d, J=8.2 Hz, 1H), 7.62 (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), 8.59 (s, 1H), 8.64 (m, 1H), 8.75 (m, 1H), 9.45 (s, 1H), 9.58 (s, 1H), 10.38 (s, 1H), 10.54 (s, 1H). (m/z)=534 (M+H)+.

Provenance & Evidence