5-BROMOIMIDAZO[1,2-A]PYRIDINE-2-CARBALDEHYDE

To a solution of X4-019-4 (3.0 g, 1.73 mol) and DME (120 ml) was added X4-019-4a (5.6 g, 3.03 mol) in one portion at room temperature, the reaction mixture was stirred at65 °C for 4 hours. After being cooled down to 10 °C, the mixture was stirred for 1 hour and filtered. After washing with DME, The filtered solid was suspended in DME (120 ml) and 2 M HC1 aq. (120 ml), and stirred overnight at 75 °C. After being cooled down to 10 °C, the mixture was neutralized with 3 M NaOH aq. to pH = 8 and filtered. The filtered cake was washed with water and dried in vacuum at 50 °C to give X4-019-5 as an off-white solid (2.81 g, 72percent yield). LC-MS (Agilent LCMS 1200-6110, Mobile Phase: from 95percent [water + 0.05percent TFA] and 5percent [CH3CN + 0.05percent TFA] to 0percent [water + 0.05percent TFA] and 100percent [CH3CN + 0.05 percent TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95percent [water + 0.05percent TFA] and 5percent [CH3CN + 0.05percent TFA] in 0.05 mm and under this condition for 0.7 mi. Purity: 94.5percent, Rt = 1.26 mm; MS Calcd.: 223.96; MS Found: 225.1 [M+H]tThe reactor is charged with 2-amino-6-bromopyridine (3.0 Kg, 17.3 mol) and dimethoxyethane ( 12 Liters) and stirred under nitrogen. 1, 1, 3-Trichloroacetone (5.6 Kg, 30.3 mol) is added to the 25° C solution in a single portion and the reaction solution is warmed to 65 To a solution of 2-amino-6-bromopyridine (10 g, 58 mmol) in ethylene glycol dimethyl ether (66 mL) was added trichloroacetone (18 mL, 173 mmol). The mixture was stirred at 7OTo a solution of X4-019-4 (3.0 g, 1.73 mol) and DME (120 ml) was added X4-019-4a (5.6 g, 3.03 mol) in one portion at room temperature, the reaction mixture was stirred at65 °C for 4 hours. After being cooled down to 10 °C, the mixture was stirred for 1 hour and filtered. After washing with DME, The filtered solid was suspended in DME (120 ml) and 2 M HC1 aq. (120 ml), and stirred overnight at 75 °C. After being cooled down to 10 °C, the mixture was neutralized with 3 M NaOH aq. to pH = 8 and filtered. The filtered cake was washed with water and dried in vacuum at 50 °C to give X4-019-5 as an off-white solid (2.81 g, 72percent yield). LC-MS (Agilent LCMS 1200-6110, Mobile Phase: from 95percent [water + 0.05percent TFA] and 5percent [CH3CN + 0.05percent TFA] to 0percent [water + 0.05percent TFA] and 100percent [CH3CN + 0.05 percent TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95percent [water + 0.05percent TFA] and 5percent [CH3CN + 0.05percent TFA] in 0.05 mm and under this condition for 0.7 mi. Purity: 94.5percent, Rt = 1.26 mm; MS Calcd.: 223.96; MS Found: 225.1 [M+H]tThe reactor is charged with 2-amino-6-bromopyridine (3.0 Kg, 17.3 mol) and dimethoxyethane ( 12 Liters) and stirred under nitrogen. 1, 1, 3-Trichloroacetone (5.6 Kg, 30.3 mol) is added to the 25° C solution in a single portion and the reaction solution is warmed to 65 To a solution of 2-amino-6-bromopyridine (10 g, 58 mmol) in ethylene glycol dimethyl ether (66 mL) was added trichloroacetone (18 mL, 173 mmol). The mixture was stirred at 7OTo a solution of X4-019-4 (3.0 g, 1.73 mol) and DME (120 ml) was added X4-019-4a (5.6 g, 3.03 mol) in one portion at room temperature, the reaction mixture was stirred at65 C for 4 hours. After being cooled down to 10 C, the mixture was stirred for 1 hour and filtered. After washing with DME, The filtered solid was suspended in DME (120 ml) and 2 M HC1 aq. (120 ml), and stirred overnight at 75 C. After being cooled down to 10 C, the mixture was neutralized with 3 M NaOH aq. to pH = 8 and filtered. The filtered cake was washed with water and dried in vacuum at 50 C to give X4-019-5 as an off-white solid (2.81 g, 72% yield). LC-MS (Agilent LCMS 1200-6110, Mobile Phase: from 95% [water + 0.05% TFA] and 5% [CH3CN + 0.05% TFA] to 0% [water + 0.05% TFA] and 100% [CH3CN + 0.05 % TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95% [water + 0.05% TFA] and 5% [CH3CN + 0.05% TFA] in 0.05 mm and under this condition for 0.7 mi. Purity: 94.5%, Rt = 1.26 mm; MS Calcd.: 223.96; MS Found: 225.1 [M+H]t

Molecular Weight:225.04
XLogP3:2.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:223.95853
Monoisotopic Mass:223.95853
Topological Polar Surface Area:34.4
Heavy Atom Count:12
Complexity:188
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes