Triethylamine → HCID 58137741, compound

Participants

Reaction Conditions

Reaction Steps

Carbon monoxide gas was charged into a pressure bottle containing a mixture of tert-butyl 4-(8-chloro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)phenylcarbamate (61C) (714 mg, 2.065 mmol), Pd(OAc)2 (185 mg, 0.826 mmol), dppp (341 mg, 0.826 mmol), Et3N (1.15 mL, 8.26 mmol), DMSO (12 mL) and MeOH (6 mL) until the pressure reached to 30 psi. The bottle was then sealed and heated at 75° C. for 4 h. After cooling to room temperature, the reaction was diluted with EtOAc, washed with water (3×), saturated aqueous NaCl, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge eluting with a gradient of EtOAc in hexanes to afford 103 mg (17%) of the title compound. HPLC/MS (Method C): retention time=1.72 min, [M+H]+=370.4; 1H NMR (500 MHz, DMSO-d6): δ 9.75 (s, 1H), 8.78 (d, J=4.95 Hz, 1H), 8.04 (d, J=4.95 Hz, 1H), 7.86 (d, J=8.80 Hz, 2H), 7.73 (d, J=8.80 Hz, 2H), 4.02 (s, 3H), 1.47 (s, 9H).

Provenance & Evidence