Imidazole → HCID 72203014, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-4-methyl-N-(4-(trifluoromethoxy)phenyl)benzamide (100 mg, 0.237 mmol), imidazole (64.6 mg, 0.95 mmol), CuI (9.04 mg, 0.048 mmol), L-proline (10.94 mg, 0.094 mmol), K2CO3 (131.2 mg, 0.95 mmol) and DMSO (250 μL) were stirred under argon for 66 h at 90° C. The RM was cooled to, diluted with DCM/EtOAc, filtered, washed with 10% aq. NaCO3 solution and brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure to give a residue which was purified by flash chromatography (RediSep® 4 g silica gel, DCM/MeOH+1% NH3 from 0% B to 10% DCM/MeOH+1% NH3) to afford the title compound. UPLC-MS (Condition 2) tR=0.9 min, m/z=362.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.23 (s, 3H) 7.12 (d, J=0.78 Hz, 1H) 7.36 (d, J=8.99 Hz, 2H) 7.49 (d, J=0.78 Hz, 1H) 7.58 (d, J=7.82 Hz, 1H) 7.84-7.90 (m, 2H) 7.90-7.93 (m, 1H) 7.93-7.95 (m, 1H) 7.98 (dd, J=7.82, 1.56 Hz, 1H) 10.41 (s, 1H).

Provenance & Evidence