N-(2-bromo-5-(3-(2-cyanopropan-2-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide → N-(2-cyano-5-(3-(2-cyanopropan-2-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Steps

A solution of N-(2-bromo-5-(3-(2-cyanopropan-2-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 64 (80 mg, 0.154 mmol), copper(I) iodide (29.3 mg, 0.154 mmol) and copper(I) cyanide (13.77 mg, 0.154 mmol) in NMP (1.5 mL) was stirred 10 min in microwave at 150° C. with cooling on. The reaction mixture was poured out in NH4Cl solution and extracted with EtOAc. Organic layer was washed (3×) with water, brine, dried, and evaporated. Purification by chromatography CH2Cl2: MeOH (9:1) and then crystallization in acetonitrile gave the title compound N-(2-cyano-5-(3-(2-cyanopropan-2-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 65 (12 mg, 16%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 7.64 (t, d=7.8 Hz, 1H), 7.80 (d, J=7.8 Hz, 1H), 7.87 (dd, J=8.6 and 1.9 Hz, 1H), 7.92-7.99 (m, 2H), 8.05 (m, 1H), 8.21 (d, J=1.9 Hz, 1H), 8.58 (s, 1H), 8.79 (d, J=2.3 Hz, 1H), 8.91 (d, J=2.3 Hz, 1H), 10.82 (s, 1H), 11.25 (s, 1H). (m/z)=467 (M+H)+.

Provenance & Evidence