Dimethylformamide → HCID 178424031, compound

Participants

Reaction Conditions

Reaction Steps

Zinc cyanide (44 mg, 0.375 mmol) was weighed into a 50 mL flask, a degassed solution of 5-bromo-2-((5,7-dimethyl-1H-indol-4-yl)methyl)-7-fluoro-1H-benzo[d]imidazole (45 mg, 0.121 mmol) in DMF (4 mL) was added followed by Pd(Ph3P)4 (14 mg, 0.012 mmol). The reaction mixture was heated at 120° C. for 2 hours. Additional portions of zinc dust, dppf, and Pd2(dba)3 were added followed by heating to 130° C. until no starting material remained by LC-MS. The reaction was diluted with EtOAc and a saturated solution of NaHCO3, then filtered through a Celite® pad. The filtrate was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (HC-B) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.98 (br. s., 1H) 7.78 (s, 1H) 7.52-7.67 (m, 1H) 7.48 (d, J=10.61 Hz, 1H) 7.24 (t, J=2.78 Hz, 1H) 6.76 (s, 1H) 6.46 (dd, J=3.03, 2.02 Hz, 1H) 4.44 (s, 2H) 2.41 (s, 3H) 2.36 (s, 3H). HRMS calculated for C19H15FN4(M+H)+ 319.1354. found 319.1361.

Provenance & Evidence