* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium carbonate In water; toluene for 1.5 h; Heating / reflux
2N Na2C03 (20 mL, 0.04 mol) was added to a suspension of aminopyridine (1) (l. OOg, 5. 78 mmol) and boronic acid (2) (1.06 g, 8. 67 mmol) in toluene (60 mL) and the mixture was purged with nitrogen gas. Bis (diphenylphosphino) ferrocenepalladium (II) chloride, dichloromethane complex [hereinafter"PdCl2 (dppf)"] (0.17 g, 0.21 mmol) was added and the mixture was refluxed under nitrogen for 1.5 hours. Ethyl acetate was added and the solution was washed with water, dried over Na2S04 and adsorbed onto silica by removal of solvent in vacuo. The residue was chromatographed on silica, eluting with MeOH/EtOAc (1: 15) to give product (3) as a powder (0. 87 g, 87percent). APCI-MS found: [M+H] +=172.
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; toluene; for 1.5h;Heating / reflux;
2N Na2C03 (20 mL, 0.04 mol) was added to a suspension of aminopyridine (1) (l. OOg, 5. 78 mmol) and boronic acid (2) (1.06 g, 8. 67 mmol) in toluene (60 mL) and the mixture was purged with nitrogen gas. Bis (diphenylphosphino) ferrocenepalladium (II) chloride, dichloromethane complex [hereinafter"PdCl2 (dppf)"] (0.17 g, 0.21 mmol) was added and the mixture was refluxed under nitrogen for 1.5 hours. Ethyl acetate was added and the solution was washed with water, dried over Na2S04 and adsorbed onto silica by removal of solvent in vacuo. The residue was chromatographed on silica, eluting with MeOH/EtOAc (1: 15) to give product (3) as a powder (0. 87 g, 87percent). APCI-MS found: [M+H] +=172.
With potassium carbonate;sodium 2'?(dicyclohexylphosphaneyl)?2,6?diisopropyl?[1,1'?biphenyl]?3?sulfonate; palladium diacetate; In water; at 100℃; for 12h;
A reaction container with a screw cap was charged with <strong>[84249-14-9]4-bromopyridin-2-amine</strong> (2.51 g, 14.5 mmol), pyridin-3-ylboronic acid (2.67 g, 21.8 mmol), sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3- sulfonate (0.149 g, 0.290 mmol), diacetoxypalladium (0.0326 g, 0.145 mmol) and K2CO3 (6.02 g, 43.5 mmol). A septum was attached and the container was evacuated and back filled with Ar three times. In a separate flask was charged with 30 mL H2O. The flask was degassed under vacuum for 10 minutes. The degassed H2O was then added to the reaction container, which was then flashed with Ar and capped. Heat to 1000C and stir for 12 hours. Cool to ambient temperature and extracted with EtOAc (3 x 60 mL). Combine and flash chromatography (EtOAc/MeOH 20:1) provided final product.
(7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-carbamic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
5%
With 2,6-dimethylpyridine; In 1,3-dimethyl-2-imidazolidinone; at 110℃; for 4.5h;
A solution of aminopyridine (3) (0.94 g, 5.49 mmol), ethyl chloroacetylcarbamate (1.09 g, 6.58 mmol) and 2,6-lutidine (0.76 mL, 6.58 mmol) in 1, 3-dimethyl-2-imidazolidinone (6 mL) was warmed under nitrogen at 110 C for 4.5 hours. The mixture was diluted with EtOAc and washed with water (6 times), then adsorbed onto silica by removal of solvent in vacuo. The product was chromatographed on silica. Elution with EtOAc gave foreruns, while MeOH/EtOAc (2: 23) eluted product (79 mg, 5%) as a solid, mp 248-252 C (decomposed).