Sodium Carbonate → HCID 56598977, compound

Participants

Reaction Conditions

Reaction Steps

6-amino-5-(trifluoromethyl)pyridin-3-ylboronic acid (1.677 mmol) and palladium dichlorobis triphenylphosphine (10 mol %) were added to a solution of N-(8-bromo-1-(6-methoxypyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (compound of step 5, 1.118 mmol) in dry DMF in an inert atmosphere. Saturated Na2CO3 (0.3 ml) was added to the reaction mixture and the resulting solution was heated at 110° C. for 3 h. The solvent was removed; the crude material was extracted in EtOAc, washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the crude solid was purified (silica gel column, EtOAc/MeOH as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 9.20 (s, 1H), 8.66 (d, J=3 Hz, 1H), 8.38 (d, J=3 Hz, 1H), 8.22 (m, 2H), 8.06 (dd, J=9 Hz, 3 Hz, 1H), 7.55 (s, 1H), 7.19 (d, J=9 Hz, 1H), 7.03 (d, J=3 Hz, 1H), 6.79 (s, 2H), 3.99 (s, 3H), 3.84 (s, 3H); MS (m/z): 491.2 (M+1)+.

Provenance & Evidence