Sodium Carbonate → 2-Amino-5-[2-(3,4-dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3,4-dimethoxy-phenyl)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole (0.1 g, 0.258 mmol, 1 eq), 2-amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinonitrile (0.11 g, 0.449 mmol, 1.74 eq), PdCl2(Ph3P)2 (36 mg, 0.052 mmol, 0.2 eq) and Na2CO3 (2 M aqueous solution, 0.5 mL) in dioxane was heated at 110° C. for 2.5 h. The reaction was cooled down to it and solvents were removed under reduced pressure. The residue was treated with water, sonicated and then filtered. The solid was washed with water, Et2O, Et2O/MeOH (9:1), and dried. The residue was purified on silica gel (isolute flash Si II, DCM/MeOH 5 to 10% MeOH and biotage, MeOH/DCM, 0% to 10%) to give the desired product (21 mg, 22%). HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=4.68 min, [M+H]+ m/z 379.1; 1H NMR (300 MHz, DMSO) δ 8.91 (d, J=2.4 Hz, 1H), 8.45 (d, J=2.4 Hz, 1H), 7.72 (s, 2H), 7.56 (dd, J=8.4, 2.1 Hz, 1H), 7.48 (d, J=2.1 Hz, 1H), 7.17 (m, 3H), 3.89 (s, 3H), 3.86 (s, 3H).

Provenance & Evidence